Asymmetric tandem conjugate addition-allylation of chiral (p-tolylsulfinyl)pyrrolyl cinnamoyl amide

被引：14

作者：

Arai, Y ^{[1
]}

Kasai, M ^{[1
]}

Ueda, K ^{[1
]}

Masaki, Y ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Gifu 5028585, Japan

来源：

SYNTHESIS-STUTTGART | 2003年 / 10期

关键词：

tandem reactions; conjugate addition reactions; chiral sulfoxide; cuprate; diastereoselectivity;

D O I：

10.1055/s-2003-40510

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alkylation by allyl halides of the intermediate enolate, prepared in situ by conjugate addition of di-p-tolylcuprate to chiral (p-tolylsulfinyl)pyrrolyl cinnamoyl amide, gave the (2R,3R)adducts as the major products with 81% to 94% de's. Methanoylsis of the products afforded the corresponding methyl esters, together with efficient recovery of the chiral sulfinyl auxiliary without loss of optical purity.

引用

页码：1511 / 1516

页数：6

共 18 条

[1] 1,6-asymmetric induction during the conjugate addition of arylcopper reagents to a chiral sulfinyl-substituted pyrrolyl α,β-unsaturated amide [J].