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基于α-单取代硝基乙酸酯的反应方法学研究
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摘要
具有四取代碳手性中心的α-季碳氨基酸结构单元广泛存在于天然产物和药物分子中。通过不对称催化的方法高效构建α-季碳氨基酸的α位季碳手性中心是目前的研究热点之一。本论文主要从α-取代的硝基乙酸酯出发,研究α-季碳氨基酸衍生物的合成新方法。全文主要分为以下三个部分:
     1)首次实现了a-取代硝基乙酸酯与偶氮二甲酸叔丁酯的不对称催化的α-胺化反应。在1,1,2,2-四氧乙烷作为溶剂,-20或-40℃的低温条件下,利用手性叔胺-氢键双功能催化剂β-ICD取得了较好的反应结果,产物的ee值高达93%。底物的普适性考察发现,α-脂肪族取代的硝基乙酸酯的反应较为顺利。但α-芳香族取代的硝基乙酸酯参与的反应,无论是产率还是对映选择性都不太理想。产物通过转化,可用于含α-季碳氨基酸结构的四取代肼衍生物的合成。
     2)首次实现了在40℃及无需外加催化剂的条件下,甲醇作为溶剂促进的一锅法α-脂肪或芳香族取代的硝基乙酸酯、甲醛水溶液以及胺类化合物的三组分Mannich反应。其中胺类化合物可以是芳香族或脂肪族伯胺以及仲胺,手性伯胺化合物也能很好的反应,但非对映选择性较差。该反应为α-胺基-β2,2-氨基酸衍生物的合成提供了一个较好的方法。反应的产物可进一步转化成一些含有α-季碳结构的p-氨基酸衍生物以及咪唑酮化合物。并通过核磁分析与理论计算的方法对甲醇作为溶剂促进的反应机理进行了初步研究。另外也初步尝试了α-甲基取代的硝基乙酸酯与预先制备的亚甲基希夫碱的不对称催化的反应,但几乎没有观察到对映选择性。
     3)以K3P04作为催化剂,实现了α-脂肪或芳香族取代硝基乙酸酯与价廉易得的多聚甲醛的羟甲基化反应。利用叔胺-羟基双功能催化剂对该反应的不对称催化研究进行了首次尝试,最高取得71%的ee值。在此基础上,设计合成了双核叔胺-膦酰胺双功能催化剂,并考察了其在羟甲基化反应中的初步应用情况。反应产物可通过转化,合成一系列α-取代丝氨酸衍生物及噁唑啉酮化合物。
C"-tetrasubstituted a-amino acids bearing a quaternary stereogenic carbon center at the a position are widely presented in natural products, drugs and pharmaceutically active compounds. The catalytic enantioselective synthesis of Cα-tetrasubstituted a-amino acid is of current research interest. This thesis focuses on the direct functionalization of a-substituted nitroacetates using different electrophiles, to furnish Cα-tetrasubstituted a-amino acid derivatives, which includes three parts:
     1) The first example of catalytic asymmetric amination of a-substituted nitroacetates using di-tert-butyl azodicarboxylate as the electrophile is developed. The simple and easily available bifunctional Br(?)nsted acid-base catalyst β-ICD is identified as be a highly enantioselective catalyst for the amination of a-aliphatic substituted substrates, with up to93%ee achieved using1,1,2,2-tetrachloroethane or CH2C12at-20or-40℃. Although a-phenylnitroacetates are also able to participate in this reaction with less hindered azodicarboxylates such as diethyl azodicarboxylate, the enantioselectivity of the corresponding product is not satisfactory. The amination product could be converted to tetrasubstituted chiral hydrazines.
     2) The first example of a highly efficient "catalyst-free" aminomethylation of both a-alkyl and aryl substituted nitroacetates in methanol is developed. A wide range of structurally diverse amines are tolerated, such as aniline derivatives and aliphatic amine. Chiral primary amines afford the corresponding products in good yields, albeit with poor diastereoselectivity. The versatility of the products is demonstrated by their facile conversion to the corresponding Cα-tetrasubstituted α,β-diamino acids-derived imidazolidinones and other useful building blocks. The high efficiency of this catalyst-free transformation is revealed by NMR spectroscopy studies and theoretical calculations.
     3) A highly efficient hydroxymethylation of both a-alkyl and aryl substituted nitroacetates catalyzed by only1mol%of K3PO4has been studied. The products could be further transformed to the corresponding quaternary a-substitued serine-derived oxazolidinone and aziridine. We also develop the first example of asymmetric catalytic version, and up to71%ee was achieved by using parafonn aldehyde as electrophile. In order to improve enantioselectivity, a series of newly chiral dual-core tertiary amine-phosphoramide catalysts have been synthesized from commercial available cinchona alkaloids, which are examined in this hydroxymethylation, but only moderate enantioselectivity was obtained.
引文
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