1,5-asymmetric induction in boron-mediated aldol reactions of β-alkoxy methylketones

被引：22

作者：

Dias, Luiz C. ^{[1
]}

de Marchi, Anderson A. ^{[1
]}

Ferreira, Marco A. B. ^{[1
]}

Aguilar, Andrea M. ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, BR-13084971 Campinas, SP, Brazil

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 16期

关键词：

D O I：

10.1021/jo8009165

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Good levels of substrate-controlled, 1,5-syn-stereoinduction are obtained in boron-mediated aldol reactions of beta-trichloromethyl-beta-alkoxy and beta-trifluoromethyl-beta-alkoxy methylketones with achiral aldehydes, independent of the nature of the beta-alkoxy protecting group (TBS or PMB). In the case of boron aldol reactions of beta-aryl-beta-alkoxy methylketones, the 1,5-anti-adducts were obtained with high levels of diastereoselectivity only with a beta-OPMB group.

引用

页码：6299 / 6311

页数：13

共 66 条

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