Catalytic, enantioselective [4+2]-cycloadditions of ketene enolates and o-quinones:: Efficient entry to chiral, α-oxygenated carboxylic acid derivatives

被引：86

作者：

Bekele, T ^{[1
]}

Shah, MH ^{[1
]}

Wolfer, J ^{[1
]}

Abraham, CJ ^{[1
]}

Weatherwax, A ^{[1
]}

Lectka, T ^{[1
]}

机构：

[1] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 06期

关键词：

D O I：

10.1021/ja058077g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report catalytic, enantioselective [4 + 2]-cycloadditions of o-quinones with ketene enolates (derived from readily available acid chlorides) using cinchona alkaloid derivatives as catalysts to produce products in high enantiomeric excess (ee) and good to excellent yields. The thermodynamic driving force for these reactions is due in part to the restoration of aromaticity to the products. The resulting chiral, bicycloadducts can be synthetically manipulated in a variety of useful ways, for example to provide a flexible synthesis of α-oxygenated carboxylic acid derivatives. Copyright © 2006 American Chemical Society.

引用

页码：1810 / 1811

页数：2

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