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
收藏
页码：5453 / 5456
页数：4
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