Triflic acid-catalyzed additions of 2-alkoxycarbonyl allylboronates to aldehydes. Study of scope and mechanistic investigation of the reaction stereochemistry

被引：56

作者：

Elford, Tim G. ^{[1
]}

Arimura, Yuichiro ^{[1
]}

Yu, Siu Hong ^{[1
]}

Hall, Dennis G. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 04期

关键词：

D O I：

10.1021/jo062151b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The substrate scope and the effect of substrate on the observed inversion of stereoselectivity in the triflic acid-catalyzed allylboration reaction between 2-alkoxycarbonyl allylboronates and aldehydes are presented. A mechanistic investigation is described so as to confirm the involvement of a carbocation intermediate as the source of stereochemical inversion. This methodology allows a facile access to beta,gamma-disubstituted five-membered ring lactones with an exo-methylene at the alpha-position.

引用

页码：1276 / 1284

页数：9

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