Boron-mediated aldol reaction of carboxylic esters

被引：68

作者：

Abiko, A ^{[1
]}

机构：

[1] Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 6068585, Japan

来源：

ACCOUNTS OF CHEMICAL RESEARCH | 2004年 / 37卷 / 06期

关键词：

D O I：

10.1021/ar030249w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This Account outlines the unique features of the boron-mediated aldol reaction of carboxylic esters, which include (i) facile isomerization of E-enolate to Z-enolate and (ii) formation of a doubly borylated enolate upon enolization of acetate esters. The first carbon-bound boron enolates were spectroscopically characterized, and they appeared to be responsible for these unique properties. Furthermore, complementary anti- and syn-selective boron-mediated asymmetric aldol reactions of chiral propionate esters have been developed. A novel double aldol reaction of acetate esters has been discovered, and a plausible mechanism of the double aldol reaction is proposed.

引用

页码：387 / 395

页数：9

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