Formation of disubstituted β-lactones using bifunctional catalysis

被引：81

作者：

Calter, MA ^{[1
]}

Tretyak, OA

Flaschenriem, C

机构：

[1] Wesleyan Univ, Dept Chem, Middletown, CT 06459 USA

[2] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 09期

关键词：

D O I：

10.1021/ol050411q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acid chlorides and aromatic aldehydes react in the presence of a stoichiometric amount of a tertiary amine and catalytic amounts of a cinchona alkaloid derivative and a Lewis acid to produce beta-lactones in high diastereo- and enantioselectivity. The sense of the diastereoselectivity depends on the substitution of the acid chloride, with the reactions of aliphatic acid chlorides giving predominantly the trans-isomer and those of alkoxyacetyl chlorides favoring formation of the cis-isomer.

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页码：1809 / 1812

页数：4

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