Recoverable chiral sulfoxide:: remote asymmetric induction in Lewis acid-promoted Diels-Alder reaction of chiral sulfinyl-substituted pyrrolyl α,β-unsaturated enones

被引：11

作者：

Arai, Y ^{[1
]}

Masuda, T ^{[1
]}

Masaki, Y ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Gifu 5028585, Japan

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 15期

关键词：

D O I：

10.1039/a902181g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-[2-(p-Tolylsulfinyl)]pyrrolyl alpha,beta-unsaturated enones served as efficient dienophiles in the Diels-Alder reaction, where the use of aluminium chloride or a lanthanide triflate effected the cycloaddition with cyclopentadiene, affording the endo adduct with high diastereoselectivity. In particular, for the sulfinyl dienophile, the chiral auxiliary (i.e. the sulfinyl pyrrole) was recovered after use without any loss of optical purity.

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收藏

页码：2165 / 2170

页数：6

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