官能团化的亚烃基环丙烷衍生物反应选择性的调控研究
摘要
当今有机合成方法学研究跨入了反应选择性控制的时代。选择具有多个反应位点或多个官能团的底物,调控和优化其反应的选择性来构建复杂分子已经成为有机合成方法学的热点之一。
亚烃基环丙烷及其衍生物是指双键和三元环碳原子直接相连的一类高张力活性分子,它具有多个反应位点。在过去的几十年间,大量文献报道了过渡金属及路易斯酸催化亚烃基环丙烷构建复杂结构分子的反应。然而,正是由于多反应位点这个特点,在同一个反应条件下,反应往往会因缺乏选择性导致多个不同产物的生成,例如有对双键的加成,或者三元环直键及侧键的断裂等产物,因而研究它的反应选择性的控制具有挑战性。最近在三元环上或者双键上引入适当官能团的策略越来越受有机合成化学家的关注。原则上讲在引入官能团的导向作用下,高张力的三元环可以发生选择性的切断和重组,从而可以很好地控制反应的区域选择性和立体选择性。
本论文的工作是基于亚烃基环丙烷具有多个反应位点的特性,通过在亚烃基环丙烷三元环上或者在双键端位引入合适官能团的策略,发展了一系列具有高度区域和立体选择性的反应来构建各种环状复杂分子。
论文的主要内容包括以下几个方面：
1.我们研究了在路易斯酸氯化锌作用下的(E)-2-亚烃基环丙基甲醛与酰氯发生氧酰化,继而选择性发生三元环侧键断裂,进行扩环重排,立体选择性的生成了双官能团化的亚烃基环丁烷衍生物。合成的环丁烷衍生物进一步经环氧化,频哪醇重排,酯消除反应一步生成了环戊烯酮化合物。如果使用(Z)-2-亚烃基环丙基甲醛与酰氯反应,则发生氧酰化三元环直键断裂开环反应,生成共轭二烯化合物。
2.我们发现了有机硒诱导的2-亚烃基环丙基甲醛的自由基反应和亲电环合反应,选择性地生成1-萘醛衍生物和3-氧杂并[3.1.0]环己-2-醇类衍生物。有机硒试剂的性质在这个反应中起了决定性作用。
3.我们发展了一种新颖的过渡金属催化下酮羰基取代亚乙烯基环丙烷选择性碳碳键断裂扩环反应,生成高活性的呋喃并环丁烯化合物。在外加氧化剂DMP控制下,呋喃并环丁烯化合物可以定向生成亚烃基环丁酮衍生物。合成的环丁酮衍生物在三氟甲磺酸酐的作用下,进一步发生四元环缩环反应,生成3-螺环丙基-2(3H)呋喃酮衍生物。若反应在CuCl,500℃反应体系下,呋喃并环丁烯化合物将转化成结构复杂的6-螺环丙基-3a,7a-并环丁烷二氢苯并呋喃酮衍生物。我们通过连续核磁跟踪的方法,观察到了中间体,提出了合理的反应机理。
4.我们发现了羰基取代亚乙烯基环丙烷与三苯基磷的磷羟化现象,并且初步研究了该反应的适用范围和反应机理。
The development of novel reactions with high regio- and stereoselectivity for construction of complex molecules is a hot topic in organic synthesis. Recently, we have witnessed tremendous growth in the strategies converting easily accessible starting materials to complex and interesting organic molecules.
Methylenecyclopropanes (MCPs) are highly strained but readily accessible carbocyclic molecules that have served as useful building blocks in organic synthesis. In the past decades, mounting attention has been paid to the transition metal- or Lewis acid-catalyzed reactions of MCPs, which have been employed for the construction of complex and interesting organic molecules. However, an attractive but often troublesome feature of MCPs is their multi-forms of reactivities leading to the formation of a variety of different products. Thus, controlling the regio- and stereoselectivity in reactions of MCPs is a formidable challenge in organic synthesis.
Recently, MCPs with functional groups attached to a cyclopropyl ring or C=C bond have received considerable attention. In principle, the presence of functional groups may facilitate the selective cleavage of C-C bonds of MCPs, thus delicately tuning the regio- and stereoselectivity of the reactions.
We have developed the following reactions:
Firstly, we disclosed the ZnCl2-mediated reactions of (E)-2-(arylmethylene)-cyclopropylaldehyde with various acyl chlorides providing a novel method for stereoselective synthesis of bifunctional methlylenecyclobutanes via a proximal-bond cleavage process. Nevertheless, when (Z)-2-(arylmethylene)cyclopropylaldehyde was employed, the reactions gave 1,3-conjugated dienes through distal-bond cleavage. On the other hand, we realized an interesting route to cyclopentenones from bifunctional methlylenecyclobutanes via a process of epoxidation, pinacol-type ring enlargement and subsequent elimination.
Secondly, we have observed a ring-opening intramolecular radical cyclization and an electrophilic cyclization reaction of (E)-2-(arylmethylene)cyclopropylaldehyde, affording a controlled synthesis of 1-naphthaldehydes and 3-oxabicyclo[3.1.0] hexan-2-ols. The properties of organo-selenium reagents such as PhSeSePh, N-PSP, PhSeBr and PhSeCl may play an important role in the reactions.
Thirdly, we have developed a cyclization of 3-cyclopropylideneprop-2-en-1-ones in the presence ofπ-philic metals leading to furan-fused cyclobutenes, which is a versatile intermediate for further elaboration. Application of PdCl2 with additional oxidant DMP or CuCl at 50℃led to a highly selective formation of the functionalized 2-alkylidenecyclobutanones and 6,7a-dihydrobenzofuran-7(3aH)-ones with one spiro-three-membered ring and one four-membered ring from cyclopropylideneallenyl ketones directly. Furthermore, we provided a clean route to 2(3H)-furanones with a spiro-three-membered ring at the 3-position from 2-alkylidenecyclobutanones. Possible mechanism is proposed on the basis of the series of NMR experiments which lead to the observation of key intermediates.
We have also found the phosphor-hydroxylation reaction of 3-cyclopropylidene-prop-2-en-1-ones. On the basis of O18 labeling experiment, a plausible reaction mechanism was proposed.
亚烃基环丙烷及其衍生物是指双键和三元环碳原子直接相连的一类高张力活性分子,它具有多个反应位点。在过去的几十年间,大量文献报道了过渡金属及路易斯酸催化亚烃基环丙烷构建复杂结构分子的反应。然而,正是由于多反应位点这个特点,在同一个反应条件下,反应往往会因缺乏选择性导致多个不同产物的生成,例如有对双键的加成,或者三元环直键及侧键的断裂等产物,因而研究它的反应选择性的控制具有挑战性。最近在三元环上或者双键上引入适当官能团的策略越来越受有机合成化学家的关注。原则上讲在引入官能团的导向作用下,高张力的三元环可以发生选择性的切断和重组,从而可以很好地控制反应的区域选择性和立体选择性。
本论文的工作是基于亚烃基环丙烷具有多个反应位点的特性,通过在亚烃基环丙烷三元环上或者在双键端位引入合适官能团的策略,发展了一系列具有高度区域和立体选择性的反应来构建各种环状复杂分子。
论文的主要内容包括以下几个方面：
1.我们研究了在路易斯酸氯化锌作用下的(E)-2-亚烃基环丙基甲醛与酰氯发生氧酰化,继而选择性发生三元环侧键断裂,进行扩环重排,立体选择性的生成了双官能团化的亚烃基环丁烷衍生物。合成的环丁烷衍生物进一步经环氧化,频哪醇重排,酯消除反应一步生成了环戊烯酮化合物。如果使用(Z)-2-亚烃基环丙基甲醛与酰氯反应,则发生氧酰化三元环直键断裂开环反应,生成共轭二烯化合物。
2.我们发现了有机硒诱导的2-亚烃基环丙基甲醛的自由基反应和亲电环合反应,选择性地生成1-萘醛衍生物和3-氧杂并[3.1.0]环己-2-醇类衍生物。有机硒试剂的性质在这个反应中起了决定性作用。
3.我们发展了一种新颖的过渡金属催化下酮羰基取代亚乙烯基环丙烷选择性碳碳键断裂扩环反应,生成高活性的呋喃并环丁烯化合物。在外加氧化剂DMP控制下,呋喃并环丁烯化合物可以定向生成亚烃基环丁酮衍生物。合成的环丁酮衍生物在三氟甲磺酸酐的作用下,进一步发生四元环缩环反应,生成3-螺环丙基-2(3H)呋喃酮衍生物。若反应在CuCl,500℃反应体系下,呋喃并环丁烯化合物将转化成结构复杂的6-螺环丙基-3a,7a-并环丁烷二氢苯并呋喃酮衍生物。我们通过连续核磁跟踪的方法,观察到了中间体,提出了合理的反应机理。
4.我们发现了羰基取代亚乙烯基环丙烷与三苯基磷的磷羟化现象,并且初步研究了该反应的适用范围和反应机理。
The development of novel reactions with high regio- and stereoselectivity for construction of complex molecules is a hot topic in organic synthesis. Recently, we have witnessed tremendous growth in the strategies converting easily accessible starting materials to complex and interesting organic molecules.
Methylenecyclopropanes (MCPs) are highly strained but readily accessible carbocyclic molecules that have served as useful building blocks in organic synthesis. In the past decades, mounting attention has been paid to the transition metal- or Lewis acid-catalyzed reactions of MCPs, which have been employed for the construction of complex and interesting organic molecules. However, an attractive but often troublesome feature of MCPs is their multi-forms of reactivities leading to the formation of a variety of different products. Thus, controlling the regio- and stereoselectivity in reactions of MCPs is a formidable challenge in organic synthesis.
Recently, MCPs with functional groups attached to a cyclopropyl ring or C=C bond have received considerable attention. In principle, the presence of functional groups may facilitate the selective cleavage of C-C bonds of MCPs, thus delicately tuning the regio- and stereoselectivity of the reactions.
We have developed the following reactions:
Firstly, we disclosed the ZnCl2-mediated reactions of (E)-2-(arylmethylene)-cyclopropylaldehyde with various acyl chlorides providing a novel method for stereoselective synthesis of bifunctional methlylenecyclobutanes via a proximal-bond cleavage process. Nevertheless, when (Z)-2-(arylmethylene)cyclopropylaldehyde was employed, the reactions gave 1,3-conjugated dienes through distal-bond cleavage. On the other hand, we realized an interesting route to cyclopentenones from bifunctional methlylenecyclobutanes via a process of epoxidation, pinacol-type ring enlargement and subsequent elimination.
Secondly, we have observed a ring-opening intramolecular radical cyclization and an electrophilic cyclization reaction of (E)-2-(arylmethylene)cyclopropylaldehyde, affording a controlled synthesis of 1-naphthaldehydes and 3-oxabicyclo[3.1.0] hexan-2-ols. The properties of organo-selenium reagents such as PhSeSePh, N-PSP, PhSeBr and PhSeCl may play an important role in the reactions.
Thirdly, we have developed a cyclization of 3-cyclopropylideneprop-2-en-1-ones in the presence ofπ-philic metals leading to furan-fused cyclobutenes, which is a versatile intermediate for further elaboration. Application of PdCl2 with additional oxidant DMP or CuCl at 50℃led to a highly selective formation of the functionalized 2-alkylidenecyclobutanones and 6,7a-dihydrobenzofuran-7(3aH)-ones with one spiro-three-membered ring and one four-membered ring from cyclopropylideneallenyl ketones directly. Furthermore, we provided a clean route to 2(3H)-furanones with a spiro-three-membered ring at the 3-position from 2-alkylidenecyclobutanones. Possible mechanism is proposed on the basis of the series of NMR experiments which lead to the observation of key intermediates.
We have also found the phosphor-hydroxylation reaction of 3-cyclopropylidene-prop-2-en-1-ones. On the basis of O18 labeling experiment, a plausible reaction mechanism was proposed.
引文
(1)(a) Hassall, C. H.; Reyle, K. Biochem. J.1955,60,334. (b) Fowden, L.; Pratt, H. M. Phytochemistry 1973,12,1677.
(2)Grey, D. O.; Fowden, L. Biochem. J.1962,82,385.
(3)Gragson, J. T.; Greenlee, K. W.; Derfer, J. M.; Boord, C. E. J. Am. Chem. Soc. 1953,75,3344.
(4)Nemoto, T.; Ojika, M.; Sakagami, Y. Tetrahedron Lett.1997,38,5667.
(5)Dolbier, W. R., Jr.; Seabury, M.; Daly, D.; Smart, B. E. J. Org. Chem.1986,51, 974.
(6)(a) de Meijere, A.; Wessjohann, L. Synlett 1990,20. (b) Wessjohann, L.; Skatteb(?)l, L.; de Meijere, A. J. Chem. Soc. Chem. Commun.1990,574.
(7)(a) Heiner, T.; Michalski, S.; Gerke, K.; Kuchta, G.; Buback, M.; de Meijere, A. Synlett 1995,355. (b) Heiner, T.; Kozhushkov, S. I.; Noltemeyer, M.; Haumann, T.; Boese. R.; de Meijere, A. Tetrahedron 1996,52,12185.
(8)(a) Vilsmaier. E.; Baumheier, R. Chem. Ber.1989,122,1285. (b) Vilsmaier, E.; Weber, S.; Weidner, J. J. Org. Chem.1987,52,4921.
(9)Cordero, F. M.; Barile, I.; De Sarlo, F.; Brandi, A. Tetrahedron Lett.1999,40, 6657.
(10)Crandall, J. K.; Conover, W. W.; Komin, J. B. J. Org. Chem.1975,40,2042.
(11)For some of the typical reports on the DMCP, see:(a) Nakamura, M.; Yoshikai, N.; Toganoh, M.; Nakamura, E. Synlett 2001,1030. (b) Nakamura, M.; Yoshikai, N.; Nakamura, E. Chem. Lett.2002,146. (c) Zhou, S.; Burger, C.; Chu, B.; Sawamura, M.; Nagahama, N.; Toganoh, M.; Hackler, U. E.; Isobe, H.; Nakamura, E. Science 2001, 291,1944. (d) Nakamura, E.; Isobe, H.; Tomita, N.; Sawamura, M.; Jinno, S.; Okayama, H. Angew. Chem., Int. Ed.2000,39,4254. (e) Isobe, H.; Sugiyama, S.; Fukui, K-i.; Iwasawa, Y.; Nakamura, E. Angew. Chem., Int. Ed.2001,40,3364. (f) Nakamura, M.; Toganoh, M.; Wang, X. Q.; Yamago, S.; Nakamura, E. Chem. Lett. 2000,664. (g) Nakamura, M.; Toganoh, M.; Ohara, H.; Nakamura, E. Org. Lett.1999, 1,7.
(12)Vilsmaier, E.; Baumheier, R.; Lemmert, M. Synthesis 1990,995.
(13)Hu, B.; Zhu, J.; Xing, S.; Fang, J.; Du, D.; Wang, Z. Chem. Eur. J.2009,15,324.
(14)Crandall, J. K.; Conover, W. W. J. Org. Chem.1978,43,3533.
(15)Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999,55,8833.
(16)Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem.2001,66, 270.
(17)Li, W.; Yuan, W.; Pindi S.; Shi M.; Li G. Org. Lett.2010,12,920.
(18)Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998,54,7203.
(19)Ma, S.; Lu, L.; Zhang, J. J. Am. Chem. Soc.2004,126,9645.
(20)Saito, S.; Masuda, M.; Komagawa, S. J. Am. Chem. Soc.2004,126,10540.
(21)Delgado, A.; Rodrigues, J. R.; Castedo, L.; Mascarenas, J. L. J. Am. Chem. Soc. 2003,125,9282.
(22)Lopez, F.; Delgado, A.; Rodrigues, J. R.; Castedo, L.; Mascarenas, J. L. J. Am. Chem. Soc.2004,126,10262
(23)Chen, W.; Cao, J.; Huang, X. Org. Lett.,2008,10,5537.
(24)Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc.1996,118,10676.
(25)Suginome, M.; Ito, Y. J. Organomet. Chem.2003,680,43.
(26)(a) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett.1999,40 3045. (b) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett.2000,41, 1615.
(27)(a) Rajamaki, S.; Kilburn, J. D. J. Chem. Soc. Chem. Commun.2005,1637. (b) Patient, L.; Berry, M. B.; Killburn, D. Tetrahedron Lett.2003,44,1015. (c) Patient, L.; Berry, M.; Coles, S. J.; Hursthouse, M. B.; Kilburn, D. J. Chem. Commun.,2003, 2552.
(28)(a) Lautens, M.; Han, W.; Liu, J. H. C. J. Am. Chem. Soc.2003,125,4028. (b) Scott, M. E.; Han, W.; Lautens, M. Org. Lett.2004,6,3309. (c) Taillier, C.; Lautens, M. Org. Lett.2007,9,591. (d) Scott, M. E.; Lautens, M. Org. Lett.2005,7,3045. (e) Lautens, M.; Han, W. J. Am. Chem. Soc.2002,124,6312.
(29)Scott, M. E.; Schwarz, C. A.; Lautens, M. Org. Lett.2006,8,5521.
(30)Yao, L.-F.; Wei, Y.; Shi, M. J. Org. Chem.2009,74,9466.
(31)Huang, X.; Zhou, H. Org. Lett.,2002,4,4419.
(32)Hu, B.; Xing, S.; Wang, Z. Org. Lett.,2008,10,5481.
(33)Wu, L.; Shi, M. Chem. Eur. J.2010,16,1149.
(34)(a) Notzel, M. W.; Labahn, T.; Es-Sayed, M.; de Meijere, A. Eur. J. Org. Chem. 2001,3025. (b) Notzel, M. W.; Tamm, M.; Labahn, T.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. J. Org. Chem.2000,65,3850.
(35)Chen, W.; Huang, X.; Zhou, H. Synlett 2004,329.
(36)Notzel, M. W.; Rauch, K.; Labahn, T.; de Meijere, A. Org. Lett.2002,4,839.
(37)Lu, L.; Chen, G.; Ma, S. Org. Lett.2006,8,835.
(38)Tang, X.-Y; Shi, M. J. Org. Chem.2009,74,5983.
(39)Watson, F. C.; Kilburn, J. D. Tetrahedron Lett.2000,41,10341.
(40)Penfold, D. J.; Pike, K.; Genge, A.; Anson, M.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett.2000,41,10347.
(41)Tian, G-Q.; Shi, M. Org. Lett.2007,9,2405.
(42)Fu, W.; Huang, X. Synlett 2007,321.
(43)Tang, X.-Y; Shi, M. J. Org. Chem.2010,75,902.
(44)Tang, X.-Y.; Wei, Y.; Shi, M. Org. Lett.2010,12,5120.
(45)Hu, B.; Jiang, L.; Ren, J.; Wang, Z. Eur. J. Org. Chem.2010,1358.
(46)Satoh, T.; Kawase, Y.; Yamakawa, K. Bull. Chem. Soc. Jpn.1991,64,1129.
(47)(a) Kakiuchi, K.; Ue, M.; Tsukahara, H.; Shimizu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc.1989,111,3707. (b) Kakiuchi, K.; Fukunaga, K.; Matsuo, F.; Ohnishi, Y.; Tobe, Y. J. Org. Chem.1991,56,6742. (c) Kakiuchi, K.; Nakamura, I.; Matsuo, F.; Nakata, M.; Ogura, M.; Tobe, Y.; Kurosawa, H. J. Org. Chem.1995,60,3318. (d) Kakiuchi, K.; Horiguchi, T.; Minato, K.; Tobe, Y.; Kurosawa, H. J. Org. Chem.1995,60,6557.
(48)Jiang, X.; Cheng, X.; Ma, S. Angew. Chem. Int. Ed.2006,45,8009.
(49)Kurahashi, T.; de Meijere A. Angew. Chem. Int. Ed.2005,44,7881.
(50)Markham, J. P.; Staben, S. T.; Toste F. D. J. Am. Chem. Soc.2005,127,9708.
(51)Shi, M.; Tian, G.-Q. Tetrahedron Lett.2006,47,8059.
(52)Huang, X.; Yang, Y. Org. Lett.2007,9,1667.
(53)Jackson; W. P.; Ley, S. V.; Morton, J. A. J. Chem. Soc. Chem. Commun.1980, 1028.
(54)Fragale, G.; Wirth, T. Eur. J. Org. Chem.1998,1361.
(55)(a) Herndon, J. W.; Harp, J. J. Tetrahedron Lett.1992,33,6243. (b) Herndon, J. W.; Harp, J. J. J. Organometal. Chem.1990,393.
(56)Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc.1973,95,2697.
(57)Huang, X.; Xiong, Z.-C. Chem. Commun.2003,1714.
(58)Wirth, T.; Kulicke K. J.; Fragale, G. J. Org. Chem.1996,61,2686.
(59)Liu, L.-P.; Shi, M. Chem. Commun.2004,2878.
(60)Yu, L.; Huang, X. Synlett 2006,13,2136.
(61)Liu, L.-P.; Shi, M. J. Org. Chem.2004,69,2805.
(62)Fu, W.; Huang X. Tetrahedron Lett.2008,49,562.
(63)Ma, S.; Lu L. J. Org. Chem.2005,70,7629.
(64)Fiirstner, A.; Davies, P. W.; Gress T.J. Am. Chem. Soc.2005,127,8244.
(65)Nieto-Oberhuber, C.; Lo'pez, S.; M. Echavarren, A. J. Am. Chem. Soc.2005,127, 6178.
(66)Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc.2005,127,11260.
(67)Xu, H.; Zhang, W.; Shu, D.; Werness, J. B.; Tang, W. Angew. Chem. Int. Ed.2008, 47,8933.
(68)Xiao, F.; Wang, J. J. Org. Chem.2006,71,5789.
(69)Shi, M.; Liu, L.-P.; Tang, J. J. Am. Chem. Soc.2006,128,7430.
(70)Li, C.-W.; Pati, K.; Lin, G.-Y.; Abu Sohel, S. Md.; Hung, H.-H.; Liu R.-S. Angew. Chem. Int. Ed.2010,49,9891.
(71)Saito, K.; Sogou, H.; Suga, T.; Kusama, H.; Iwasawa, N. J. Am. Chem. Soc.2011, 133,689.
(72)Le, Corre M.; Hercouet, A.; Bessieres, B. J. Org. Chem.1994,59,5483.
(73)(a) Shao, L.-X.; Li, J.; Wang, B.-Y.; Shi, M. Eur. J. Org. Chem.2010,6448. (b) 付维军博士论文,浙江大学,2007.
(74)Sharpless, K. B.; Young, M. W. J. Org. Chem.1975,40,947.
(75)Bridges, Alexander J.; Fischer, John W. J. Org. Chem.1984,49,2954.
(76)Parr, W. J. E. J. Chem. Soc. Perkin Trans.11981,12,3002.
(77)Nicolaou, K. C.; Petatis, N. A.; Claremon, D. A. Tetrahedron 1985,41,4835.
(78)(a) Siebeneicher, H.; Doye, S. Eur. J. Org. Chem.2002,1213. (b) Yang, C.; Lin, M; Liao H.; Liu, R. Chem. Eur. J.2010,16,2696.
(2)Grey, D. O.; Fowden, L. Biochem. J.1962,82,385.
(3)Gragson, J. T.; Greenlee, K. W.; Derfer, J. M.; Boord, C. E. J. Am. Chem. Soc. 1953,75,3344.
(4)Nemoto, T.; Ojika, M.; Sakagami, Y. Tetrahedron Lett.1997,38,5667.
(5)Dolbier, W. R., Jr.; Seabury, M.; Daly, D.; Smart, B. E. J. Org. Chem.1986,51, 974.
(6)(a) de Meijere, A.; Wessjohann, L. Synlett 1990,20. (b) Wessjohann, L.; Skatteb(?)l, L.; de Meijere, A. J. Chem. Soc. Chem. Commun.1990,574.
(7)(a) Heiner, T.; Michalski, S.; Gerke, K.; Kuchta, G.; Buback, M.; de Meijere, A. Synlett 1995,355. (b) Heiner, T.; Kozhushkov, S. I.; Noltemeyer, M.; Haumann, T.; Boese. R.; de Meijere, A. Tetrahedron 1996,52,12185.
(8)(a) Vilsmaier. E.; Baumheier, R. Chem. Ber.1989,122,1285. (b) Vilsmaier, E.; Weber, S.; Weidner, J. J. Org. Chem.1987,52,4921.
(9)Cordero, F. M.; Barile, I.; De Sarlo, F.; Brandi, A. Tetrahedron Lett.1999,40, 6657.
(10)Crandall, J. K.; Conover, W. W.; Komin, J. B. J. Org. Chem.1975,40,2042.
(11)For some of the typical reports on the DMCP, see:(a) Nakamura, M.; Yoshikai, N.; Toganoh, M.; Nakamura, E. Synlett 2001,1030. (b) Nakamura, M.; Yoshikai, N.; Nakamura, E. Chem. Lett.2002,146. (c) Zhou, S.; Burger, C.; Chu, B.; Sawamura, M.; Nagahama, N.; Toganoh, M.; Hackler, U. E.; Isobe, H.; Nakamura, E. Science 2001, 291,1944. (d) Nakamura, E.; Isobe, H.; Tomita, N.; Sawamura, M.; Jinno, S.; Okayama, H. Angew. Chem., Int. Ed.2000,39,4254. (e) Isobe, H.; Sugiyama, S.; Fukui, K-i.; Iwasawa, Y.; Nakamura, E. Angew. Chem., Int. Ed.2001,40,3364. (f) Nakamura, M.; Toganoh, M.; Wang, X. Q.; Yamago, S.; Nakamura, E. Chem. Lett. 2000,664. (g) Nakamura, M.; Toganoh, M.; Ohara, H.; Nakamura, E. Org. Lett.1999, 1,7.
(12)Vilsmaier, E.; Baumheier, R.; Lemmert, M. Synthesis 1990,995.
(13)Hu, B.; Zhu, J.; Xing, S.; Fang, J.; Du, D.; Wang, Z. Chem. Eur. J.2009,15,324.
(14)Crandall, J. K.; Conover, W. W. J. Org. Chem.1978,43,3533.
(15)Tsukada, N.; Shibuya, A.; Nakamura, I.; Kitahara, H.; Yamamoto, Y. Tetrahedron 1999,55,8833.
(16)Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem.2001,66, 270.
(17)Li, W.; Yuan, W.; Pindi S.; Shi M.; Li G. Org. Lett.2010,12,920.
(18)Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A.; Pleuss, N. Tetrahedron 1998,54,7203.
(19)Ma, S.; Lu, L.; Zhang, J. J. Am. Chem. Soc.2004,126,9645.
(20)Saito, S.; Masuda, M.; Komagawa, S. J. Am. Chem. Soc.2004,126,10540.
(21)Delgado, A.; Rodrigues, J. R.; Castedo, L.; Mascarenas, J. L. J. Am. Chem. Soc. 2003,125,9282.
(22)Lopez, F.; Delgado, A.; Rodrigues, J. R.; Castedo, L.; Mascarenas, J. L. J. Am. Chem. Soc.2004,126,10262
(23)Chen, W.; Cao, J.; Huang, X. Org. Lett.,2008,10,5537.
(24)Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc.1996,118,10676.
(25)Suginome, M.; Ito, Y. J. Organomet. Chem.2003,680,43.
(26)(a) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett.1999,40 3045. (b) Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett.2000,41, 1615.
(27)(a) Rajamaki, S.; Kilburn, J. D. J. Chem. Soc. Chem. Commun.2005,1637. (b) Patient, L.; Berry, M. B.; Killburn, D. Tetrahedron Lett.2003,44,1015. (c) Patient, L.; Berry, M.; Coles, S. J.; Hursthouse, M. B.; Kilburn, D. J. Chem. Commun.,2003, 2552.
(28)(a) Lautens, M.; Han, W.; Liu, J. H. C. J. Am. Chem. Soc.2003,125,4028. (b) Scott, M. E.; Han, W.; Lautens, M. Org. Lett.2004,6,3309. (c) Taillier, C.; Lautens, M. Org. Lett.2007,9,591. (d) Scott, M. E.; Lautens, M. Org. Lett.2005,7,3045. (e) Lautens, M.; Han, W. J. Am. Chem. Soc.2002,124,6312.
(29)Scott, M. E.; Schwarz, C. A.; Lautens, M. Org. Lett.2006,8,5521.
(30)Yao, L.-F.; Wei, Y.; Shi, M. J. Org. Chem.2009,74,9466.
(31)Huang, X.; Zhou, H. Org. Lett.,2002,4,4419.
(32)Hu, B.; Xing, S.; Wang, Z. Org. Lett.,2008,10,5481.
(33)Wu, L.; Shi, M. Chem. Eur. J.2010,16,1149.
(34)(a) Notzel, M. W.; Labahn, T.; Es-Sayed, M.; de Meijere, A. Eur. J. Org. Chem. 2001,3025. (b) Notzel, M. W.; Tamm, M.; Labahn, T.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. J. Org. Chem.2000,65,3850.
(35)Chen, W.; Huang, X.; Zhou, H. Synlett 2004,329.
(36)Notzel, M. W.; Rauch, K.; Labahn, T.; de Meijere, A. Org. Lett.2002,4,839.
(37)Lu, L.; Chen, G.; Ma, S. Org. Lett.2006,8,835.
(38)Tang, X.-Y; Shi, M. J. Org. Chem.2009,74,5983.
(39)Watson, F. C.; Kilburn, J. D. Tetrahedron Lett.2000,41,10341.
(40)Penfold, D. J.; Pike, K.; Genge, A.; Anson, M.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett.2000,41,10347.
(41)Tian, G-Q.; Shi, M. Org. Lett.2007,9,2405.
(42)Fu, W.; Huang, X. Synlett 2007,321.
(43)Tang, X.-Y; Shi, M. J. Org. Chem.2010,75,902.
(44)Tang, X.-Y.; Wei, Y.; Shi, M. Org. Lett.2010,12,5120.
(45)Hu, B.; Jiang, L.; Ren, J.; Wang, Z. Eur. J. Org. Chem.2010,1358.
(46)Satoh, T.; Kawase, Y.; Yamakawa, K. Bull. Chem. Soc. Jpn.1991,64,1129.
(47)(a) Kakiuchi, K.; Ue, M.; Tsukahara, H.; Shimizu, T.; Miyao, T.; Tobe, Y.; Odaira, Y.; Yasuda, M.; Shima, K. J. Am. Chem. Soc.1989,111,3707. (b) Kakiuchi, K.; Fukunaga, K.; Matsuo, F.; Ohnishi, Y.; Tobe, Y. J. Org. Chem.1991,56,6742. (c) Kakiuchi, K.; Nakamura, I.; Matsuo, F.; Nakata, M.; Ogura, M.; Tobe, Y.; Kurosawa, H. J. Org. Chem.1995,60,3318. (d) Kakiuchi, K.; Horiguchi, T.; Minato, K.; Tobe, Y.; Kurosawa, H. J. Org. Chem.1995,60,6557.
(48)Jiang, X.; Cheng, X.; Ma, S. Angew. Chem. Int. Ed.2006,45,8009.
(49)Kurahashi, T.; de Meijere A. Angew. Chem. Int. Ed.2005,44,7881.
(50)Markham, J. P.; Staben, S. T.; Toste F. D. J. Am. Chem. Soc.2005,127,9708.
(51)Shi, M.; Tian, G.-Q. Tetrahedron Lett.2006,47,8059.
(52)Huang, X.; Yang, Y. Org. Lett.2007,9,1667.
(53)Jackson; W. P.; Ley, S. V.; Morton, J. A. J. Chem. Soc. Chem. Commun.1980, 1028.
(54)Fragale, G.; Wirth, T. Eur. J. Org. Chem.1998,1361.
(55)(a) Herndon, J. W.; Harp, J. J. Tetrahedron Lett.1992,33,6243. (b) Herndon, J. W.; Harp, J. J. J. Organometal. Chem.1990,393.
(56)Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc.1973,95,2697.
(57)Huang, X.; Xiong, Z.-C. Chem. Commun.2003,1714.
(58)Wirth, T.; Kulicke K. J.; Fragale, G. J. Org. Chem.1996,61,2686.
(59)Liu, L.-P.; Shi, M. Chem. Commun.2004,2878.
(60)Yu, L.; Huang, X. Synlett 2006,13,2136.
(61)Liu, L.-P.; Shi, M. J. Org. Chem.2004,69,2805.
(62)Fu, W.; Huang X. Tetrahedron Lett.2008,49,562.
(63)Ma, S.; Lu L. J. Org. Chem.2005,70,7629.
(64)Fiirstner, A.; Davies, P. W.; Gress T.J. Am. Chem. Soc.2005,127,8244.
(65)Nieto-Oberhuber, C.; Lo'pez, S.; M. Echavarren, A. J. Am. Chem. Soc.2005,127, 6178.
(66)Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc.2005,127,11260.
(67)Xu, H.; Zhang, W.; Shu, D.; Werness, J. B.; Tang, W. Angew. Chem. Int. Ed.2008, 47,8933.
(68)Xiao, F.; Wang, J. J. Org. Chem.2006,71,5789.
(69)Shi, M.; Liu, L.-P.; Tang, J. J. Am. Chem. Soc.2006,128,7430.
(70)Li, C.-W.; Pati, K.; Lin, G.-Y.; Abu Sohel, S. Md.; Hung, H.-H.; Liu R.-S. Angew. Chem. Int. Ed.2010,49,9891.
(71)Saito, K.; Sogou, H.; Suga, T.; Kusama, H.; Iwasawa, N. J. Am. Chem. Soc.2011, 133,689.
(72)Le, Corre M.; Hercouet, A.; Bessieres, B. J. Org. Chem.1994,59,5483.
(73)(a) Shao, L.-X.; Li, J.; Wang, B.-Y.; Shi, M. Eur. J. Org. Chem.2010,6448. (b) 付维军博士论文,浙江大学,2007.
(74)Sharpless, K. B.; Young, M. W. J. Org. Chem.1975,40,947.
(75)Bridges, Alexander J.; Fischer, John W. J. Org. Chem.1984,49,2954.
(76)Parr, W. J. E. J. Chem. Soc. Perkin Trans.11981,12,3002.
(77)Nicolaou, K. C.; Petatis, N. A.; Claremon, D. A. Tetrahedron 1985,41,4835.
(78)(a) Siebeneicher, H.; Doye, S. Eur. J. Org. Chem.2002,1213. (b) Yang, C.; Lin, M; Liao H.; Liu, R. Chem. Eur. J.2010,16,2696.