SmI2-Promoted Reformatsky-Type Reaction and Acylation of Alkyl 1-Chlorocyclopropanecarboxylates

被引：23

作者：

Nagano, Takao ^{[1
]}

Motoyoshiya, Jiro ^{[1
]}

Kakehi, Akikazu ^{[1
]}

Nishii, Yoshinori ^{[1
]}

机构：

[1] Shinshu Univ, Dept Chem, Fac Text Sci & Technol, Nagano 3868567, Japan

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 23期

关键词：

D O I：

10.1021/ol8022038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of HMPA in THF, highly stereoselective Sml(2)-promoted substitutions of alkyl 1-chlorocyclopropanecarboxylates 1 using various ketones, aldehydes (Reformatsky-type reaction), and acyl chlorides (acylation) proceeded to give trans-adducts (2 or 5) in good to high yield with excellent trans-stereoselectivity (trans-add/cis-add = > 99/1). The Reformatsky-type reaction of 1 with aldehydes and unsymmetrical ketones proceeded with moderate diastereoselectivity (re-face-adduct/si-face-adduct = 60/40-75/25).

引用

页码：5453 / 5456

页数：4

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