二芳基甲烷化合物的合成方法研究及DNA催化的Aldol反应研究
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摘要
本文主要论述了1,1—二芳基甲基类化合物及其衍生物的合成新方法。此类化合物广泛存在于具有重要生理活性的天然产物和化学药物中。
本文可分为六个部分,第一、二部分简介1,1—二芳基甲基类化合物及其合成方法;第三部分我们使用便宜易得的苄醇作为起始底物,研究了1,1—二芳基甲基类化合物的高效合成方法;第四部分我们则使用了苯乙烯作为作为起始底物,研究了1,1—二芳基甲基类化合物的高效合成方法;第五部分进行了DNA在有机化学反应中应用的研究,如Aldol反应。第六部分简述了部分抗HIV药物的设计、合成研究。
一、以苄醇和苯乙烯为原料合成1,1—二芳基甲基类化合物
在研究合成方法学中,我们使用了绿色环保的无溶剂反应的策略,以易得的起始原料如苄醇和苯乙烯快速地合成了所要的目标产物。研究探索阶段使用了InCl_3作为催化剂,实现了目标产物的合成。这种方法尽管具有高效快速的优点,而且我们还制备了InCl_3的非均相可循环催化剂,但是仍然具有一定的缺点和局限性,例如必要的加热,重金属的使用等。为了克服这些缺点,在后期的研究中,我们发展了非金属催化剂—碘—催化的氢化芳基化反应。此法更加快速、简洁、高效,成本低廉,这些优点使得本法不仅对实验室制备,而且对工业化生产具有很高的应用价值。在研究中,我们还对机理进行了一定的讨论和研究。
二、DNA催化的Aldol反应研究
DNA广泛存在于生物体内,是重要的生命物质基础,对生物的生长、发育和繁殖等有重要的作用。DNA具有右手螺旋结构和良好的几何学特性,是一种充满活力的生物高聚物,它可以耐得住一定范围的pH、温度和溶剂环境。近几年,DNA逐渐引起有机化学研究工作者们的兴趣,不断被用于有机反应催化领域。
Alodol反应是一类重要的形成碳—碳键的有机合成反应。已经有很多关于此反应的优秀工作。生物学方法如醛缩酶以及具有催化活性的抗体被广泛用于Aldol反应,其中不少能进行手性催化。不过还未有将DNA直接作为催化剂用于Aldol反应的报道,我们最初设想是将DNA直接用作手性催化剂来实现手性Aldol反应,不过目前试验结果表明,未能得到手性产物,不过我们实现非手性Aldol反应的催化。
三、三类抗HIV药物的设计、合成研究
在研究生期间,还承担了部分抗HIV药物的设计、合成研究。合成的潜在药物主要有三类:香豆素类,三胺基类和吲哚类。
The new methods to synthesize 1,1-diarylalkane and its derivatives are described in this dissertation.1,1-diarylalkane moieties exist extensively in bioactive natural products and chemic pharmaceuticals.
Six parts are included in this dissertation.In the first and second part,we briefly review the application and synthesis of 1,1-diarylalkane and its derivatives.We develop an efficient method to synthesize 1,1-diarylalkane and its derivatives with accessible starting material,benzyl alcohol in the third part.Then we also develop another synthesis route to obtain 1,1-diarylalkane and its derivatives with styrene.In the fifth part,we investigate the catalytic ability of DNA in Aldol reaction.Finally,the design and synthesis of some anti-HIV compounds are also briefly described.
1.The synthesis of 1,1-diarylalkane and its derivatives with benzyl alcohol and styrene
To develop a synthetic method for 1,1-diarylalkane and its derivatives,we apply the strategy of solvent-free reaction condition with accessible starting materials such as benzyl alcohol and styrene.Firstly,InCl_3 with high catalytic activity for the formation of C-C bond was employed in this reaction to afford 1,1-diarylalkane derivatives.In spite of the high efficiency and the recycle of InCl_3,the preparartion involving InCl_3 has some shortcomings such as indispensable heating and the application of heavy metal,etc.Therefore,a novel molecular iodine-catalyzed hydroarylation is developed under metal-free.Such virtues as efficiency,simple manipulation and low cost endow this reaction as an engaging route for the synthesis of the valuable 1,1-diarylalkanes with great applicable value.Besides,preliminary mechanism study is also carried out.
2.DNA-catalyzed Aldol reaction
DNA exists extensively in organism,a important and basic life substance,that is in close relationship with the growth,development and reproducibility.With its characteristic fight-handed helix structure and well-defined geometry and the tolerance for a range of pH value and temperature,DNA has been employed in organic reactions by an ever-increasing number of chemists.
Aldol reaction is an important carbon-carbon bond formation reaction widely used in organic synthesis.There were lots of outstanding reports about aldol reaction. Aldolase and antibody were applied into aldol reaction,and some of them could realize asymmetric aldol reaction.Here we describe the direct use of DNA as the catalyst to carry out aldol reaction in the presence of water.
3.The synthesis of three kinds of anti-HIV compounds
In addition,the preparation of some anti-HIV compounds is also described including eoumarin-type compounds,triamidocyanogen-type compounds and indole-type compounds.
本文可分为六个部分,第一、二部分简介1,1—二芳基甲基类化合物及其合成方法;第三部分我们使用便宜易得的苄醇作为起始底物,研究了1,1—二芳基甲基类化合物的高效合成方法;第四部分我们则使用了苯乙烯作为作为起始底物,研究了1,1—二芳基甲基类化合物的高效合成方法;第五部分进行了DNA在有机化学反应中应用的研究,如Aldol反应。第六部分简述了部分抗HIV药物的设计、合成研究。
一、以苄醇和苯乙烯为原料合成1,1—二芳基甲基类化合物
在研究合成方法学中,我们使用了绿色环保的无溶剂反应的策略,以易得的起始原料如苄醇和苯乙烯快速地合成了所要的目标产物。研究探索阶段使用了InCl_3作为催化剂,实现了目标产物的合成。这种方法尽管具有高效快速的优点,而且我们还制备了InCl_3的非均相可循环催化剂,但是仍然具有一定的缺点和局限性,例如必要的加热,重金属的使用等。为了克服这些缺点,在后期的研究中,我们发展了非金属催化剂—碘—催化的氢化芳基化反应。此法更加快速、简洁、高效,成本低廉,这些优点使得本法不仅对实验室制备,而且对工业化生产具有很高的应用价值。在研究中,我们还对机理进行了一定的讨论和研究。
二、DNA催化的Aldol反应研究
DNA广泛存在于生物体内,是重要的生命物质基础,对生物的生长、发育和繁殖等有重要的作用。DNA具有右手螺旋结构和良好的几何学特性,是一种充满活力的生物高聚物,它可以耐得住一定范围的pH、温度和溶剂环境。近几年,DNA逐渐引起有机化学研究工作者们的兴趣,不断被用于有机反应催化领域。
Alodol反应是一类重要的形成碳—碳键的有机合成反应。已经有很多关于此反应的优秀工作。生物学方法如醛缩酶以及具有催化活性的抗体被广泛用于Aldol反应,其中不少能进行手性催化。不过还未有将DNA直接作为催化剂用于Aldol反应的报道,我们最初设想是将DNA直接用作手性催化剂来实现手性Aldol反应,不过目前试验结果表明,未能得到手性产物,不过我们实现非手性Aldol反应的催化。
三、三类抗HIV药物的设计、合成研究
在研究生期间,还承担了部分抗HIV药物的设计、合成研究。合成的潜在药物主要有三类:香豆素类,三胺基类和吲哚类。
The new methods to synthesize 1,1-diarylalkane and its derivatives are described in this dissertation.1,1-diarylalkane moieties exist extensively in bioactive natural products and chemic pharmaceuticals.
Six parts are included in this dissertation.In the first and second part,we briefly review the application and synthesis of 1,1-diarylalkane and its derivatives.We develop an efficient method to synthesize 1,1-diarylalkane and its derivatives with accessible starting material,benzyl alcohol in the third part.Then we also develop another synthesis route to obtain 1,1-diarylalkane and its derivatives with styrene.In the fifth part,we investigate the catalytic ability of DNA in Aldol reaction.Finally,the design and synthesis of some anti-HIV compounds are also briefly described.
1.The synthesis of 1,1-diarylalkane and its derivatives with benzyl alcohol and styrene
To develop a synthetic method for 1,1-diarylalkane and its derivatives,we apply the strategy of solvent-free reaction condition with accessible starting materials such as benzyl alcohol and styrene.Firstly,InCl_3 with high catalytic activity for the formation of C-C bond was employed in this reaction to afford 1,1-diarylalkane derivatives.In spite of the high efficiency and the recycle of InCl_3,the preparartion involving InCl_3 has some shortcomings such as indispensable heating and the application of heavy metal,etc.Therefore,a novel molecular iodine-catalyzed hydroarylation is developed under metal-free.Such virtues as efficiency,simple manipulation and low cost endow this reaction as an engaging route for the synthesis of the valuable 1,1-diarylalkanes with great applicable value.Besides,preliminary mechanism study is also carried out.
2.DNA-catalyzed Aldol reaction
DNA exists extensively in organism,a important and basic life substance,that is in close relationship with the growth,development and reproducibility.With its characteristic fight-handed helix structure and well-defined geometry and the tolerance for a range of pH value and temperature,DNA has been employed in organic reactions by an ever-increasing number of chemists.
Aldol reaction is an important carbon-carbon bond formation reaction widely used in organic synthesis.There were lots of outstanding reports about aldol reaction. Aldolase and antibody were applied into aldol reaction,and some of them could realize asymmetric aldol reaction.Here we describe the direct use of DNA as the catalyst to carry out aldol reaction in the presence of water.
3.The synthesis of three kinds of anti-HIV compounds
In addition,the preparation of some anti-HIV compounds is also described including eoumarin-type compounds,triamidocyanogen-type compounds and indole-type compounds.
引文
(1)Khadilkar,B.M.;Borkar,S.D.Chem.Technol.Biotechnol.1998,71,209.
(2)Martinez,A.G.;Bareina,J.O.;Heras,M.R.C.;Cerezzo,A.F.Org.Lett.,2000,2,1377.
(3)Sun,H.H.;Paul,V.J.;Fenical,W.Phytochemistry,1983,22,743.
(4)Elz,S.;Kramer,K.;Leschke,C.;Schunack,W.Eur.J.Med.Chem.2000,35,41.
(1) Kleiderer, E. C; Korwfeld, E. C. J. Org. Chem. 1948,13,455.
(2) Kursanov, D. N.; Parnes, Z. N.; Loim, N. M. Synthesis, 1974, 633.
(3) Olah, G A.; Arvanaghi, M.; Ohannesian, L. Synthesis, 1986,770.
(4) (a) Ono, A.; Suzuki, N.; Kamimura, J. Synthesis, 1987, 736; (b) Box, V. G. S.; Meleties, P. C. Tetrahedron Lett. 1998,39, 7059.
(5) Ram, S.; Spicer, L. D. Tetrahedron Lett. 1988,29,3741.
(6) Kogan, V.; Aizenshtat, Z.; Neumann, R. Angew. Chem. Int. Ed. 1999,38,3331.
(7) Miyai, T.; Ueba, M.; Baba, A. Synthesis, 1999,182.
(8) Hicks, L. D.; Han, J. K.; Fry, A. J. Tetrahedron Lett. 2000, 41, 7817.
(9) Hattori, K.; Sajiki, H.; Hirota, K. Tetrahedron Lett. 2001,57,4817.
(10)Chandrasekhar, S.; Reddy, Ch. R.; Babu, B. N. J. Org. Chem. 2002, 67,9080.
(11)Ishimoto, K.; Mitoma, Y.; Nagashima, S.; Tashiro, H.; Prakash, G K. S.; Olah, G. A.; Tashiro M. Chem. Commun. 2003, 514.
(12)Hatano, B.; Tagaya, H. Tetrahedron Lett. 2003, 44, 6331.
(13)Zaccheria, F.; Ravasio, N.; Ercolic, M.; Allegrini P. Tetrahedron Lett. 2005,46, 7743.
(14)Prakash, G. K. S.; Mathew, T.; Marinez, E. R.; M. Esteves, P.; Rasul, G.; Olah, G. A. J. Org. Chem. 2006, 71,3952.
(15)Nimmagadda, R. D. ;McRae, C. Tetrahedron Lett. 2006, 47,5755.
(16)Huston, R. C.; Friedemann, T. E. J. Am. Chem. Soc. 1916,38,2527.
(17)McKenna, J. F.; Sowa, F. J. J. Am. Chem. Soc. 1937,59,470.
(18)Simons, J. H.; Archer, S. J. Am. Chem. Soc. 1940, 62,1623.
(19) Yamauchi, T.; Hattori, K.; Mizutaki, S.; Tamaki, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1986,59, 3617.
(20)Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S.-I. Synlett. 1996,557.
(21)Gihani, M. T. E.; Heaney, H.; Shuhaibar, K. F. Synlett. 1996, 871.
(22)Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S.-I. J. Org. Chem. 1997, 62, 6997.
(23)Choudhury, J.; Podder, S.; Roy, S. J. Am. Chem. Soc. 2005,127,6162.
(24)Rueping, M.; Nachtsheim, B. J.; Ieawsuwan, W. Adv. Synth. Catal. 2006,348, 1033.
(25)Clark, J. H.; Kybett, A. P.; Macquarrie, D. J.; Barlow, S. J.; Landon, P. J. Chem. Soc., Chem. Commun. 1989, 71,1353.
(26)Eynde, J. J. V.; Mayence, A.; Haverbeke, Y. V. Tetrahedron Lett. 1995,36, 3133.
(27)Miyai, T.; Onishi, Y.; Baba, A. Tetrahedron 1999, 55,1017.
(28)Ogoshi, S.; Nakashima, H.; Shimonaka, K.; Kurosawa, H. J. Am. Chem. Soc. 2001,123, 8626.
(29)Rahman, M. T.; Nahar, S. K. J. Organomet. Chem. 1987,329,133.
(30)Lang, R.-J. D.; Hooijdonk, M. J. M. V.; Brandsma, L. Tetrahedron 1998,54, 2953.
(31)Frisch, A. C; Shaikh, N.; Zapf, A.; Beller, M. Angew. Chem. Int. Ed. 2002, 41, 4056.
(32)Dubbaka, S. R.; Vogel, P. Tetrahedron Lett. 2006, 47,3345.
(33)Gall, E. L.; Troupel, M.; Nedelec, J.-Y. Tetrahedron 2006, 62, 9953.
(34)(a) Bishop, M. J.; McNutt, R. W. Bioorg. Med. Chem. Lett. 1995,5,1311; (b) Hamlin, K. E.; Weston, A. W.; Fischer, F. E.; Michaels, R. J., Jr. J. Am. Chem. Soc. 1949, 71,2731; (c) Ide, W. S.; Lorz, E.; Phillips, A. P.; Russell, P. B.; Baltzly, R.; Blumfeld, R. J. Am. Chem. Soc. 1959,81,459; (d) Spencer, C. M.; Foulds, D.; Peters, D. H. Drugs 1993,46,1055; (e) Sakurai, S.; Ogawa, N.; Suzuki, T.; Kato, K.; Ohashi, T.; Yasuda, S.; Kato, H.; Ito, Y. Chem. Pharm. Bull. 1996,44,765.
(35)Tsai, F.-Y.; Lin,B.-N.; Chen,M.-J.; Mou,C-Y.;Liu, S.-T.; Tetrahedron 2007,55,4304.
(36)Fukuzawa, S.-I.; Tsuchimoto, T.; Hiyama T. J. Org. Chem. 1997, 62,151.
(37)Martinez, A. G.; Barcina, J. O.; Heras, M. D. R. C; Cerezo, A. D. F. Org. Lett. 2000,2,1377.
(38)Moss, R. A.; Fede, J.-M.; Yan, S. J. Am. Chem. Soc. 2000,122,9878.
(39)Perez, I; Sestelo, J. P.; Sarandeses, L. A. J. Am. Chem. Soc. 2001,123,4155.
(40)Molander, G. A.; Ito, T. Org. Lett. 2001,3,393.
(41)Itami, K.; Mineno, M.; Kamei, T.; Yoshida, J.-I. Org. Lett. 2002,4,3635.
(42)Molander, G. A.; Elia, M. J. Org. Chem. 2006, 71, 9198.
(43)Negishi, E.-I.; Akiyoshi, K.; O'Connor, B.; Takagi, K.; Wu, G. Z. J. Am. Chem. Soc. 1989, 111, 3089.
(44) Yonezawa, N.; Hino, T.; Tokita, Y.; Matsuda, K.; Ikeda, T. Tetrahedron 1997,53, 14287.
(45)Adkins, H.; Cramer, H. J. Am. Chem. Soc. 1930,52,4349.
(46)Nystrom, R. F.; Berger, C. R. A. J. Am. Chem. Soc. 1958,80,2896.
(47)Maryanoff, B. E.; McComsey, D. F.; Nortey, S. O. J. Org. Chem. 1981, 46, 355.
(48)Olah, G. A.; Wu, A.-H.; Farooq, O. J. Org. Chem. 1991,56,2759.
(49)Stoner, E. J.; Cothron, D. A.; Baimer, M. K.; Roden, B. A.; Tetrahedron 1995,51, 11043.
(50)Gevorgyan, V.; Rubin, M; Benson, S.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 2000,65,6179.
(51) Yasuda, M.; Onishi, Y.; Ueba, M.; Miyai, T.; Baba, A. J. Org. Chem. 2001, 66, 7741.
(52)Gordon, P. E.; Fry, A. J. Tetrahedron Lett. 2001,42, 831.
(53)Zaccheria, F.; Ravasio, N.; Ercoli, M.; Allegrini, P. Tetrahedron Lett. 2005, 46, 7743.
(54)Islam, N.-U.; Sopher, D. W.; Utley, J. H. P. Tetrahedron 1987, 43, 959.
(55)Chowdhury, S.; Georghiou, P. E. Tetrahedron Lett. 1999, 40, 7599.
(56)(a)Botella, L.; Najera, C. J. Organomet. Chem. 2002, 663, 46; (b) Botella, L.; Najera, C. Angew. Chem. Int. Ed. 2002, 41, 179.
(57)Chahen, L.; Doucet, H.; Santelli, M. Synlett. 2003,11,1668.
(58)(a)Hong, F.-E.; Chang, Y.-C; Chang, C.-P.; Huang, Y.-L. Dalton Trans. 2004, 157; (b) Chang, C.-P.; Huang, Y.-L.; Hong, F.-E.; Tetrahedron 2005, 61, 3835.
(59)Nobre, S. M.; Wolke, S. I.; Rosa, R. G. D.; Monteiro, A. L. Tetrahedron Lett. 2004, 45, 6527.
(60)Nobre, S. M.; Monteiro, A. L. Tetrahedron Lett. 2004,45,6527.
(61)Bandgar, B. P.; Bettigeri, S. V.; Phopase, J. Tetrahedron Lett. 2004,45, 8225.
(62)Najera, C.; Gil-Molto, J.; Karlstrom, S. Adv. Synth. Catal. 2004,346,1798.
(63)Baleizao, C.; Corma, A.; Garcia, H.; Leyva, A. J. Org. Chem. 2004, 69,439.
(64)Singh, R.; Viciu, M. S.; Kramareva, N.; Navarro, O.; Nolan, S. P. Org. Lett. 2005, 7,1829.
(65)Cwik, A.; Hell, Z.; Figueras, F. Org. Biomol. Chem. 2005,3,4307.
(66)Song, C; Ma, Y.; Chai, Q.; Ma, C; Jiang, W.; Andrus, M. B.; Tetrahedron 2005, 61,7438.
(67)Vanier, C.; Lorge, F.; Wagner, A.; Mioskowski, C. Angew. Chem. Int. Ed. 2000, 39,1679.
(68)Kuwano, R.; Yokogi, M. Org. Lett. 2005, 7,945.
(69)McLaughlin, M. Org. Lett. 2005, 7,4875.
(70)Kuwano, R.; Yokogi, M. Chem. Commun. 2005,5899.
(71)Kischel, J.; Jovel, I.; Mertins, K.; Zapf, A.; Beller, M. Org. Lett. 2006,8,19.
(72)Rueping, M.; Nachtsheim, B. J.; Scheidt, T. Org. Lett. 2006,8,3717.
(73)Sun, H.-B.; Li, B.; Hua, R.; Yin, Y. Eur. J. Org. Chem. 2006,4231.
(1)(a)Li,J.-M.;Zha,Z.-G.;Sun,L.-L.;Zhang,Y.;Wang,Z.-Y.Chem.Lett.2006,35,498;
(b)Zha,Z.-G.;Hui,A.-L.;Zhou,Y-Q.;Miao,Q.;Wang,Z.-Y.;Zhang,H.-C.Org.Lett.2005,7,1903;
(c)Zha,Z.-G.;Qiao,S.;Jiang,J.-Y.;Wang,Y.-S.;Miao,Q.;Wang,Z.-Y.Tetrahedron 2005,61,2521;
(d)Hui,A.-L.;Xu,X.-L.;Zha,Z.-G.;Zhou,C.-L.;Wang,Z.-Y.Arkivoc 2004(ⅸ),52;
(e)Zhou,C.-L;Zhou,Y.-Q.;Jiang,J.-Y.;Xie.Z.;Wang,Z.-Y.Tetrahedron Lett.2004,45,5537;
(f)Xu,X.-L.;Zha,Z.-G.;Miao,Q.;Wang,Z.-Y.Synlett 2004,1171;
(g)Zha,Z.-G.;Xie,Z.;Zhou,C.-L.;Chang,M-X.;Wang,Z.-Y.New J.Chem.2003,27,1297;
(h)Zha,Z.-G.;Zhen,X.;Zhou,C.-L.;Wang,Y.-S.;Wang,Z.-Y.Chin.J.Chem.2002,20,1477;
(i)Wang,Z.-Y.;Zha,Z.-G.;Zhou.C.-L.Org.Lett.2002,4,1683;
(j)Pan,C.F.;Zhang,Z.H.;Sun,G.J.;Wang,Z.Y.Org.Lett.2004,6,3059;
(k)Zhou,C.L.;Jiang,J.Y.;Zhou,Y.Q.;Xie,Z.;Miao,Q.;Wang,Z.Y.Lett.Org.Chem.2005,2(1),61;
(l)Pan,C.F.;Ma,Z.X.;Yu,J.;Zhang,Z.H.;Hui,A.L.;Wang,Z.Y.Synlett 2005,1922;
(m)Pan,C.F.;Yu,J.;Zhou,Y.Q.;Wang,Z.Y.;Zhou,M.M.Synlett 2006,1657.
(2)Sur,B.;Adak,M.M.;Pathak,T.;Hazra,B.;Banerjee,A.Synthesis,1985,652.
(3)(a)Tsuchimoto,T.;Tobita,K.;Hiyama,T.;Fukuzawa,S.J.Org.Chem.1997,62,6997;
(b)Nishiguchi,T.;Machida,N.;Yamamoto,E.Tetrahedron Lett.1987,28,4565;
(c)Kantam,M.L.;Santhi,P.K.;Siddiqui,M.F.Tetrahedron Lett.1993,34,1185;
(d)Lange,J.-P.;Mesters,C.M.A.Apll.Catal.A.:Gen.2001,210,247.
(4)(a)Podder,S.;Choudhury,J.;Roy,S.J..Org.Chem.2007,72,3129-3132;
(b)Rueping,M.;Nachtsheim,B.J.;Ieawsuwan,W.Adv.Synth.Catal.2006,348,1033-1037;
(c)Yamauchi,T.;Hattori,K.;Mizutaki,S.;Tamaki,K.;Uemura,S.Bull.Chem.Soc.Jpn.1986,59,3617-3620;
(d)Kotsuki,H.;Ohishi,T.;Inoue,M.;Kojima,T.Synthesis 1999,4,603-606;
(e)Noji,M.;Ohno,T.;Fuji,K.;Futaba,N.;Tajima,H.;Ishii,K.J..Org.Chem.2003,68,9340-9347.
(5)Stavber,G.;Zupan,M.;Stavber,S.Tetrahedron Lett.2006,47,8463-8466.
(1)Kischel,J.;Jovel,I.;Mertins,K.;Zapf,A.;Beller,M.Org.Lett.2006,8,19;
(b)Rueping,M.;Nachtsheim,B.J.;Scheidt,T.Org.Lett.2006,8,3717;
(c)Sun,H.-B.;Li,B.;Hua,R.;Yin,Y.Eur.J.Org.Chem.2006,4231.
(2)Selected recent examples for this reaction:
(a)Deshpande,A.B.;Bajpai,A.R.,Samant,S.D.Appl.Catal.2001,209,229;
(b)Hu,X.;Chuah,G.K.;Jaenicke,S.Appl.Catal.2001,217,1;
(c)Choudhary,V.R.;Jana,S.K.J.Catal.2001,201,225;
(d)Choudhary,V.R.;Jana,S.K.;Narkhede,V.S.Appl.Catal.2002,235,207;
(e)Shrigadi,N.B.;Shinde,A.B.;Samant,S.D.Appl.Catal.2003,252,23;
(f)Bachari,K.;Millet,J.M.M.;Benaichouba,B.;Cherifi,O.;Figueras,F.J.Catal.2004,221,55;
(g)Salavati-Niasari M.;Hasanalian,J.;Najafian,H.J.Mol.Catal.A 2004,209,209;
(h)Choudhary,V.R.;Jha,R.;Choudhari,P.A.J.Chem.Sci.2005,117(6),635;
(i)Choudhary,V.R.;Jha,R.;Narkhede,V.S.J.Mol.Catal.A 2005,239,76.
(3)(a)Pan,C.F.;Ma,Z.X.;Yu,J.;Zhang,Z.H.;Hui,A.L.;Wang,Z.Y.Synlett 2005,1922;
(b)Pan,C.F.;Yu,J.;Zhou,Y.Q.;Wang,Z.Y.;Zhou,M.M.Synlett 2006,1657.
(4)Alem,K.A.;Belder,G.;Lodder,G.;Zuihof,H.J.Org.Chem.2005,70,179.
(5)Bemasconi,S.;Orsini,F.;Sello,G.;Gennaro,P.D.Tetrahedron:Asymmetry 2004,15,1603.
(6)(a)Screttas,G.C.;Micha-Screttas,M.J.Org.Chem.1978,43,1064;
(b)Kanagasabapathy,S.;Sudalai,A.;Benicewicz,B.C.Tetrahedron Lett.2001,42,3791.
(1) Devlin, T. M. Textbook of Biochemistry with Clinical Correlations, John Wiley & Sons, New York, 1997.
(2) For reviews see: (a) Lu, Y. and Liu, J. W. Curr. Opin. Biotechnol. 2006, 17, 580; (b) Roelfes, G Mol. BioSyst. 2007, 5, 126; (c) Scherer, L. J. and Rossi, J. J. Nat. Biotechnol. 2003,21,1457; (d) Liu, J. W. and Lu, Y. J. Fluoresc. 2004, 14, 343; (e) Lu, Y. and Liu, J. W. Acc. Chem. Res. 2007,40,315; (f) May, J. P.; Ting, R.; Lermer, L.; Thomas, J. M.; Roupioz, Y. and Perrin, D. M. J. Am. Chem. Soc. 2004,126,4145; (g) Isaka, Y. Curr. Opin. Mol. Ther. 2007,9,132.
(3) (a) Kanan, M. W.; Rozenman, M. M.; Sakurai, K.; Snyder, T. M. and Liu, D. R. Nature 2004, 431, 545; (b) Li, X. Y. and Liu, D. R. Angew. Chem. Int. Ed. 2004, 43, 4848 and references therein; (c) Silverman, A. P. and Kool, E. T. Chem. Rev. 2006,106, 3775; (d) Sakurai, K.; Snyder, T. M. and Liu, D. R. J. Am. Chem. Soc. 2005,127,1660; (e) Obika, S.; Tomizu, M.; Negoro, Y; Orita, A.; Nakagawa, O. and Imanishi, T. ChemBioChem 2007, 8, 1924; (f) Oberhuber, M. and Joyce, G. F. Angew. Chem. Int. Ed. 2005, 44, 7580.
(4) (a) Miller, S. J. Nat. Biotechnol. 2004, 22, 1378; (b) Tang, Z. and Marx, A. Angew. Chem. Int. Ed. 2007, 46, 7297; (c) Rozenman, M. M. and Liu, D. R. ChemBioChem 2006, 7, 253; (d) Silverman, S. K. Org. Biomol. Chem. 2004,2, 2701; (e) Gartner, Z. J. and Liu, D. R. J. Am. Chem. Soc. 2001,123,6961.
(5) (a) Trost, B. M. Science 1991, 254, 1471; (b) Sheldon, R. A. Green Chem. 2007,9,1273.
(6) (a) Roelfes, G and Feringa, B. L. Angew. Chem. Int. Ed. 2005, 44, 3230; (b) Coquire, D.; Feringa, B. L. and Roelfes, G Angew. Chem. Int. Ed. 2007, 46, 9308; (c) Roelfes, G; Boersma, A. J. and Feringa, B. L. Chem. Commun. 2006, 635; (d) Boersma, A. J.; Feringa, B. L. and Roelfes, G. Org. Lett. 2007, 9, 3647; (e) Shibata, N.; Yasui, H.; Nakamura, S. and Toru, T. Synlett. 2007, 1153.
(7) Machajewshi, T. D.; Wong, C.-H. Angew Chem. Int. Ed. 2000, 39, 1352 and references therein.
(8) For reviews on the use of natural aldolase enzymes in synthesis see: (a) Gijsen, H. J. M.; Qiao, L; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96,443; (b) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon Press: Oxford, 1994; (c) Wymer, N.; Toone, E. J. Curr. Opin. Chem. Biol. 2000,4,110.
(9) (a) Wagner, J.; Lerner, R. A.; Barbas, C. F., III Science 1995, 270, 1797; (b) Hoffmann, T.; Zhong, G.; List, B.; Shabat, D.; Anderson, J.; Gramatikova, S.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 1998,120, 2768; (c) Zhong, G.; Lerner, R. A.; Barbas, C. F., Ill Angew. Chem. Int. Ed 1999,38,3738.
(10) Kobayashi, S.; Nagayama, S.; Busujima, T. J. Am. Chem. Soc. 1998, 120, 8287.
(2)Martinez,A.G.;Bareina,J.O.;Heras,M.R.C.;Cerezzo,A.F.Org.Lett.,2000,2,1377.
(3)Sun,H.H.;Paul,V.J.;Fenical,W.Phytochemistry,1983,22,743.
(4)Elz,S.;Kramer,K.;Leschke,C.;Schunack,W.Eur.J.Med.Chem.2000,35,41.
(1) Kleiderer, E. C; Korwfeld, E. C. J. Org. Chem. 1948,13,455.
(2) Kursanov, D. N.; Parnes, Z. N.; Loim, N. M. Synthesis, 1974, 633.
(3) Olah, G A.; Arvanaghi, M.; Ohannesian, L. Synthesis, 1986,770.
(4) (a) Ono, A.; Suzuki, N.; Kamimura, J. Synthesis, 1987, 736; (b) Box, V. G. S.; Meleties, P. C. Tetrahedron Lett. 1998,39, 7059.
(5) Ram, S.; Spicer, L. D. Tetrahedron Lett. 1988,29,3741.
(6) Kogan, V.; Aizenshtat, Z.; Neumann, R. Angew. Chem. Int. Ed. 1999,38,3331.
(7) Miyai, T.; Ueba, M.; Baba, A. Synthesis, 1999,182.
(8) Hicks, L. D.; Han, J. K.; Fry, A. J. Tetrahedron Lett. 2000, 41, 7817.
(9) Hattori, K.; Sajiki, H.; Hirota, K. Tetrahedron Lett. 2001,57,4817.
(10)Chandrasekhar, S.; Reddy, Ch. R.; Babu, B. N. J. Org. Chem. 2002, 67,9080.
(11)Ishimoto, K.; Mitoma, Y.; Nagashima, S.; Tashiro, H.; Prakash, G K. S.; Olah, G. A.; Tashiro M. Chem. Commun. 2003, 514.
(12)Hatano, B.; Tagaya, H. Tetrahedron Lett. 2003, 44, 6331.
(13)Zaccheria, F.; Ravasio, N.; Ercolic, M.; Allegrini P. Tetrahedron Lett. 2005,46, 7743.
(14)Prakash, G. K. S.; Mathew, T.; Marinez, E. R.; M. Esteves, P.; Rasul, G.; Olah, G. A. J. Org. Chem. 2006, 71,3952.
(15)Nimmagadda, R. D. ;McRae, C. Tetrahedron Lett. 2006, 47,5755.
(16)Huston, R. C.; Friedemann, T. E. J. Am. Chem. Soc. 1916,38,2527.
(17)McKenna, J. F.; Sowa, F. J. J. Am. Chem. Soc. 1937,59,470.
(18)Simons, J. H.; Archer, S. J. Am. Chem. Soc. 1940, 62,1623.
(19) Yamauchi, T.; Hattori, K.; Mizutaki, S.; Tamaki, K.; Uemura, S. Bull. Chem. Soc. Jpn. 1986,59, 3617.
(20)Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S.-I. Synlett. 1996,557.
(21)Gihani, M. T. E.; Heaney, H.; Shuhaibar, K. F. Synlett. 1996, 871.
(22)Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S.-I. J. Org. Chem. 1997, 62, 6997.
(23)Choudhury, J.; Podder, S.; Roy, S. J. Am. Chem. Soc. 2005,127,6162.
(24)Rueping, M.; Nachtsheim, B. J.; Ieawsuwan, W. Adv. Synth. Catal. 2006,348, 1033.
(25)Clark, J. H.; Kybett, A. P.; Macquarrie, D. J.; Barlow, S. J.; Landon, P. J. Chem. Soc., Chem. Commun. 1989, 71,1353.
(26)Eynde, J. J. V.; Mayence, A.; Haverbeke, Y. V. Tetrahedron Lett. 1995,36, 3133.
(27)Miyai, T.; Onishi, Y.; Baba, A. Tetrahedron 1999, 55,1017.
(28)Ogoshi, S.; Nakashima, H.; Shimonaka, K.; Kurosawa, H. J. Am. Chem. Soc. 2001,123, 8626.
(29)Rahman, M. T.; Nahar, S. K. J. Organomet. Chem. 1987,329,133.
(30)Lang, R.-J. D.; Hooijdonk, M. J. M. V.; Brandsma, L. Tetrahedron 1998,54, 2953.
(31)Frisch, A. C; Shaikh, N.; Zapf, A.; Beller, M. Angew. Chem. Int. Ed. 2002, 41, 4056.
(32)Dubbaka, S. R.; Vogel, P. Tetrahedron Lett. 2006, 47,3345.
(33)Gall, E. L.; Troupel, M.; Nedelec, J.-Y. Tetrahedron 2006, 62, 9953.
(34)(a) Bishop, M. J.; McNutt, R. W. Bioorg. Med. Chem. Lett. 1995,5,1311; (b) Hamlin, K. E.; Weston, A. W.; Fischer, F. E.; Michaels, R. J., Jr. J. Am. Chem. Soc. 1949, 71,2731; (c) Ide, W. S.; Lorz, E.; Phillips, A. P.; Russell, P. B.; Baltzly, R.; Blumfeld, R. J. Am. Chem. Soc. 1959,81,459; (d) Spencer, C. M.; Foulds, D.; Peters, D. H. Drugs 1993,46,1055; (e) Sakurai, S.; Ogawa, N.; Suzuki, T.; Kato, K.; Ohashi, T.; Yasuda, S.; Kato, H.; Ito, Y. Chem. Pharm. Bull. 1996,44,765.
(35)Tsai, F.-Y.; Lin,B.-N.; Chen,M.-J.; Mou,C-Y.;Liu, S.-T.; Tetrahedron 2007,55,4304.
(36)Fukuzawa, S.-I.; Tsuchimoto, T.; Hiyama T. J. Org. Chem. 1997, 62,151.
(37)Martinez, A. G.; Barcina, J. O.; Heras, M. D. R. C; Cerezo, A. D. F. Org. Lett. 2000,2,1377.
(38)Moss, R. A.; Fede, J.-M.; Yan, S. J. Am. Chem. Soc. 2000,122,9878.
(39)Perez, I; Sestelo, J. P.; Sarandeses, L. A. J. Am. Chem. Soc. 2001,123,4155.
(40)Molander, G. A.; Ito, T. Org. Lett. 2001,3,393.
(41)Itami, K.; Mineno, M.; Kamei, T.; Yoshida, J.-I. Org. Lett. 2002,4,3635.
(42)Molander, G. A.; Elia, M. J. Org. Chem. 2006, 71, 9198.
(43)Negishi, E.-I.; Akiyoshi, K.; O'Connor, B.; Takagi, K.; Wu, G. Z. J. Am. Chem. Soc. 1989, 111, 3089.
(44) Yonezawa, N.; Hino, T.; Tokita, Y.; Matsuda, K.; Ikeda, T. Tetrahedron 1997,53, 14287.
(45)Adkins, H.; Cramer, H. J. Am. Chem. Soc. 1930,52,4349.
(46)Nystrom, R. F.; Berger, C. R. A. J. Am. Chem. Soc. 1958,80,2896.
(47)Maryanoff, B. E.; McComsey, D. F.; Nortey, S. O. J. Org. Chem. 1981, 46, 355.
(48)Olah, G. A.; Wu, A.-H.; Farooq, O. J. Org. Chem. 1991,56,2759.
(49)Stoner, E. J.; Cothron, D. A.; Baimer, M. K.; Roden, B. A.; Tetrahedron 1995,51, 11043.
(50)Gevorgyan, V.; Rubin, M; Benson, S.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 2000,65,6179.
(51) Yasuda, M.; Onishi, Y.; Ueba, M.; Miyai, T.; Baba, A. J. Org. Chem. 2001, 66, 7741.
(52)Gordon, P. E.; Fry, A. J. Tetrahedron Lett. 2001,42, 831.
(53)Zaccheria, F.; Ravasio, N.; Ercoli, M.; Allegrini, P. Tetrahedron Lett. 2005, 46, 7743.
(54)Islam, N.-U.; Sopher, D. W.; Utley, J. H. P. Tetrahedron 1987, 43, 959.
(55)Chowdhury, S.; Georghiou, P. E. Tetrahedron Lett. 1999, 40, 7599.
(56)(a)Botella, L.; Najera, C. J. Organomet. Chem. 2002, 663, 46; (b) Botella, L.; Najera, C. Angew. Chem. Int. Ed. 2002, 41, 179.
(57)Chahen, L.; Doucet, H.; Santelli, M. Synlett. 2003,11,1668.
(58)(a)Hong, F.-E.; Chang, Y.-C; Chang, C.-P.; Huang, Y.-L. Dalton Trans. 2004, 157; (b) Chang, C.-P.; Huang, Y.-L.; Hong, F.-E.; Tetrahedron 2005, 61, 3835.
(59)Nobre, S. M.; Wolke, S. I.; Rosa, R. G. D.; Monteiro, A. L. Tetrahedron Lett. 2004, 45, 6527.
(60)Nobre, S. M.; Monteiro, A. L. Tetrahedron Lett. 2004,45,6527.
(61)Bandgar, B. P.; Bettigeri, S. V.; Phopase, J. Tetrahedron Lett. 2004,45, 8225.
(62)Najera, C.; Gil-Molto, J.; Karlstrom, S. Adv. Synth. Catal. 2004,346,1798.
(63)Baleizao, C.; Corma, A.; Garcia, H.; Leyva, A. J. Org. Chem. 2004, 69,439.
(64)Singh, R.; Viciu, M. S.; Kramareva, N.; Navarro, O.; Nolan, S. P. Org. Lett. 2005, 7,1829.
(65)Cwik, A.; Hell, Z.; Figueras, F. Org. Biomol. Chem. 2005,3,4307.
(66)Song, C; Ma, Y.; Chai, Q.; Ma, C; Jiang, W.; Andrus, M. B.; Tetrahedron 2005, 61,7438.
(67)Vanier, C.; Lorge, F.; Wagner, A.; Mioskowski, C. Angew. Chem. Int. Ed. 2000, 39,1679.
(68)Kuwano, R.; Yokogi, M. Org. Lett. 2005, 7,945.
(69)McLaughlin, M. Org. Lett. 2005, 7,4875.
(70)Kuwano, R.; Yokogi, M. Chem. Commun. 2005,5899.
(71)Kischel, J.; Jovel, I.; Mertins, K.; Zapf, A.; Beller, M. Org. Lett. 2006,8,19.
(72)Rueping, M.; Nachtsheim, B. J.; Scheidt, T. Org. Lett. 2006,8,3717.
(73)Sun, H.-B.; Li, B.; Hua, R.; Yin, Y. Eur. J. Org. Chem. 2006,4231.
(1)(a)Li,J.-M.;Zha,Z.-G.;Sun,L.-L.;Zhang,Y.;Wang,Z.-Y.Chem.Lett.2006,35,498;
(b)Zha,Z.-G.;Hui,A.-L.;Zhou,Y-Q.;Miao,Q.;Wang,Z.-Y.;Zhang,H.-C.Org.Lett.2005,7,1903;
(c)Zha,Z.-G.;Qiao,S.;Jiang,J.-Y.;Wang,Y.-S.;Miao,Q.;Wang,Z.-Y.Tetrahedron 2005,61,2521;
(d)Hui,A.-L.;Xu,X.-L.;Zha,Z.-G.;Zhou,C.-L.;Wang,Z.-Y.Arkivoc 2004(ⅸ),52;
(e)Zhou,C.-L;Zhou,Y.-Q.;Jiang,J.-Y.;Xie.Z.;Wang,Z.-Y.Tetrahedron Lett.2004,45,5537;
(f)Xu,X.-L.;Zha,Z.-G.;Miao,Q.;Wang,Z.-Y.Synlett 2004,1171;
(g)Zha,Z.-G.;Xie,Z.;Zhou,C.-L.;Chang,M-X.;Wang,Z.-Y.New J.Chem.2003,27,1297;
(h)Zha,Z.-G.;Zhen,X.;Zhou,C.-L.;Wang,Y.-S.;Wang,Z.-Y.Chin.J.Chem.2002,20,1477;
(i)Wang,Z.-Y.;Zha,Z.-G.;Zhou.C.-L.Org.Lett.2002,4,1683;
(j)Pan,C.F.;Zhang,Z.H.;Sun,G.J.;Wang,Z.Y.Org.Lett.2004,6,3059;
(k)Zhou,C.L.;Jiang,J.Y.;Zhou,Y.Q.;Xie,Z.;Miao,Q.;Wang,Z.Y.Lett.Org.Chem.2005,2(1),61;
(l)Pan,C.F.;Ma,Z.X.;Yu,J.;Zhang,Z.H.;Hui,A.L.;Wang,Z.Y.Synlett 2005,1922;
(m)Pan,C.F.;Yu,J.;Zhou,Y.Q.;Wang,Z.Y.;Zhou,M.M.Synlett 2006,1657.
(2)Sur,B.;Adak,M.M.;Pathak,T.;Hazra,B.;Banerjee,A.Synthesis,1985,652.
(3)(a)Tsuchimoto,T.;Tobita,K.;Hiyama,T.;Fukuzawa,S.J.Org.Chem.1997,62,6997;
(b)Nishiguchi,T.;Machida,N.;Yamamoto,E.Tetrahedron Lett.1987,28,4565;
(c)Kantam,M.L.;Santhi,P.K.;Siddiqui,M.F.Tetrahedron Lett.1993,34,1185;
(d)Lange,J.-P.;Mesters,C.M.A.Apll.Catal.A.:Gen.2001,210,247.
(4)(a)Podder,S.;Choudhury,J.;Roy,S.J..Org.Chem.2007,72,3129-3132;
(b)Rueping,M.;Nachtsheim,B.J.;Ieawsuwan,W.Adv.Synth.Catal.2006,348,1033-1037;
(c)Yamauchi,T.;Hattori,K.;Mizutaki,S.;Tamaki,K.;Uemura,S.Bull.Chem.Soc.Jpn.1986,59,3617-3620;
(d)Kotsuki,H.;Ohishi,T.;Inoue,M.;Kojima,T.Synthesis 1999,4,603-606;
(e)Noji,M.;Ohno,T.;Fuji,K.;Futaba,N.;Tajima,H.;Ishii,K.J..Org.Chem.2003,68,9340-9347.
(5)Stavber,G.;Zupan,M.;Stavber,S.Tetrahedron Lett.2006,47,8463-8466.
(1)Kischel,J.;Jovel,I.;Mertins,K.;Zapf,A.;Beller,M.Org.Lett.2006,8,19;
(b)Rueping,M.;Nachtsheim,B.J.;Scheidt,T.Org.Lett.2006,8,3717;
(c)Sun,H.-B.;Li,B.;Hua,R.;Yin,Y.Eur.J.Org.Chem.2006,4231.
(2)Selected recent examples for this reaction:
(a)Deshpande,A.B.;Bajpai,A.R.,Samant,S.D.Appl.Catal.2001,209,229;
(b)Hu,X.;Chuah,G.K.;Jaenicke,S.Appl.Catal.2001,217,1;
(c)Choudhary,V.R.;Jana,S.K.J.Catal.2001,201,225;
(d)Choudhary,V.R.;Jana,S.K.;Narkhede,V.S.Appl.Catal.2002,235,207;
(e)Shrigadi,N.B.;Shinde,A.B.;Samant,S.D.Appl.Catal.2003,252,23;
(f)Bachari,K.;Millet,J.M.M.;Benaichouba,B.;Cherifi,O.;Figueras,F.J.Catal.2004,221,55;
(g)Salavati-Niasari M.;Hasanalian,J.;Najafian,H.J.Mol.Catal.A 2004,209,209;
(h)Choudhary,V.R.;Jha,R.;Choudhari,P.A.J.Chem.Sci.2005,117(6),635;
(i)Choudhary,V.R.;Jha,R.;Narkhede,V.S.J.Mol.Catal.A 2005,239,76.
(3)(a)Pan,C.F.;Ma,Z.X.;Yu,J.;Zhang,Z.H.;Hui,A.L.;Wang,Z.Y.Synlett 2005,1922;
(b)Pan,C.F.;Yu,J.;Zhou,Y.Q.;Wang,Z.Y.;Zhou,M.M.Synlett 2006,1657.
(4)Alem,K.A.;Belder,G.;Lodder,G.;Zuihof,H.J.Org.Chem.2005,70,179.
(5)Bemasconi,S.;Orsini,F.;Sello,G.;Gennaro,P.D.Tetrahedron:Asymmetry 2004,15,1603.
(6)(a)Screttas,G.C.;Micha-Screttas,M.J.Org.Chem.1978,43,1064;
(b)Kanagasabapathy,S.;Sudalai,A.;Benicewicz,B.C.Tetrahedron Lett.2001,42,3791.
(1) Devlin, T. M. Textbook of Biochemistry with Clinical Correlations, John Wiley & Sons, New York, 1997.
(2) For reviews see: (a) Lu, Y. and Liu, J. W. Curr. Opin. Biotechnol. 2006, 17, 580; (b) Roelfes, G Mol. BioSyst. 2007, 5, 126; (c) Scherer, L. J. and Rossi, J. J. Nat. Biotechnol. 2003,21,1457; (d) Liu, J. W. and Lu, Y. J. Fluoresc. 2004, 14, 343; (e) Lu, Y. and Liu, J. W. Acc. Chem. Res. 2007,40,315; (f) May, J. P.; Ting, R.; Lermer, L.; Thomas, J. M.; Roupioz, Y. and Perrin, D. M. J. Am. Chem. Soc. 2004,126,4145; (g) Isaka, Y. Curr. Opin. Mol. Ther. 2007,9,132.
(3) (a) Kanan, M. W.; Rozenman, M. M.; Sakurai, K.; Snyder, T. M. and Liu, D. R. Nature 2004, 431, 545; (b) Li, X. Y. and Liu, D. R. Angew. Chem. Int. Ed. 2004, 43, 4848 and references therein; (c) Silverman, A. P. and Kool, E. T. Chem. Rev. 2006,106, 3775; (d) Sakurai, K.; Snyder, T. M. and Liu, D. R. J. Am. Chem. Soc. 2005,127,1660; (e) Obika, S.; Tomizu, M.; Negoro, Y; Orita, A.; Nakagawa, O. and Imanishi, T. ChemBioChem 2007, 8, 1924; (f) Oberhuber, M. and Joyce, G. F. Angew. Chem. Int. Ed. 2005, 44, 7580.
(4) (a) Miller, S. J. Nat. Biotechnol. 2004, 22, 1378; (b) Tang, Z. and Marx, A. Angew. Chem. Int. Ed. 2007, 46, 7297; (c) Rozenman, M. M. and Liu, D. R. ChemBioChem 2006, 7, 253; (d) Silverman, S. K. Org. Biomol. Chem. 2004,2, 2701; (e) Gartner, Z. J. and Liu, D. R. J. Am. Chem. Soc. 2001,123,6961.
(5) (a) Trost, B. M. Science 1991, 254, 1471; (b) Sheldon, R. A. Green Chem. 2007,9,1273.
(6) (a) Roelfes, G and Feringa, B. L. Angew. Chem. Int. Ed. 2005, 44, 3230; (b) Coquire, D.; Feringa, B. L. and Roelfes, G Angew. Chem. Int. Ed. 2007, 46, 9308; (c) Roelfes, G; Boersma, A. J. and Feringa, B. L. Chem. Commun. 2006, 635; (d) Boersma, A. J.; Feringa, B. L. and Roelfes, G. Org. Lett. 2007, 9, 3647; (e) Shibata, N.; Yasui, H.; Nakamura, S. and Toru, T. Synlett. 2007, 1153.
(7) Machajewshi, T. D.; Wong, C.-H. Angew Chem. Int. Ed. 2000, 39, 1352 and references therein.
(8) For reviews on the use of natural aldolase enzymes in synthesis see: (a) Gijsen, H. J. M.; Qiao, L; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96,443; (b) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon Press: Oxford, 1994; (c) Wymer, N.; Toone, E. J. Curr. Opin. Chem. Biol. 2000,4,110.
(9) (a) Wagner, J.; Lerner, R. A.; Barbas, C. F., III Science 1995, 270, 1797; (b) Hoffmann, T.; Zhong, G.; List, B.; Shabat, D.; Anderson, J.; Gramatikova, S.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 1998,120, 2768; (c) Zhong, G.; Lerner, R. A.; Barbas, C. F., Ill Angew. Chem. Int. Ed 1999,38,3738.
(10) Kobayashi, S.; Nagayama, S.; Busujima, T. J. Am. Chem. Soc. 1998, 120, 8287.