Lewis acid-catalyzed reactions of ethyl diazoacetate with aldehydes.: Synthesis of α-formyl esters by a sequence of aldol reaction and 1,2-nucleophilic rearrangement

被引：55

作者：

Kanemasa, S ^{[1
]}

Kanai, T

Araki, T

Wada, E

机构：

[1] Kyushu Univ, Inst Adv Mat Study, Kasuga, Fukuoka 8168580, Japan

[2] Kyushu Univ, Interdisciplinary Grad Sch Engn Sci, Dept Mol Sci & Technol, Kasuga, Fukuoka 8168580, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(99)00932-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ethyl diazoacetate reacts with a variety of aldehydes in the presence of a Lewis acid catalyst to give either beta-keto esters or alpha-formyl esters, the types of products mainly depending upon the nature of Lewis acid catalysts employed. Reactions catalyzed by Lewis acids such as SnCl2 and SnCl4 provide beta-keto esters via nucleophilic 1,2-hydride migration, while those catalyzed by trimethylsilyl triflate give alpha-formyl esters via migration of the substituent of the aldehyde. Reaction mechanisms are discussed. (C) 1999 Elsevier Science Ltd. All right reserved.

引用

页码：5055 / 5058

页数：4

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