A practical new chiral controller for asymmetric Diels-Alder and alkylation reactions

被引：55

作者：

Sarakinos, G ^{[1
]}

Corey, EJ ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 11期

关键词：

D O I：

10.1021/ol991007s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The enantiomerically pure hydroxy sulfones (+)- and (-)-2 have been prepared from 1,2-epoxycyclohexane by a simple and practical procedure, The acrylate esters of these alcohols undergo BCl3-catalyzed Diels-Alder reactions with a variety of dienes at -78 to -55 degrees C in CH2Cl2 or C7H8 with high dienophile face selectivity (Table 1). The chiral esters so formed are readily cleaved with recovery of the controllers (+) or (-)-2, Esters of (+) and (-)-2 can be converted to Z-potassium enolates and alkylated with high face selectivity.

引用

页码：1741 / 1744

页数：4