Simple chiral diene ligands provide high enantioselectivities in transition-metal-catalyzed conjugate addition reactions

被引：125

作者：

Okamoto, Kazuhiro ^{[1
]}

Hayashi, Tamio ^{[1
]}

Rawal, Viresh H. ^{[2
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

[2] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 19期

关键词：

D O I：

10.1021/ol801931v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral dienes possessing the bicyclo[2.2.2]octadiene framework were prepared readily through the [4 + 2] cycloaddition of (R)-alpha-phellandrene with methyl propiolate as the key step. Diene 9, substituted with a tertiary alcohol on one of the two double bonds, is prepared in just one step from the cycloadduct and is highly effective as a chiral ligand for rhodium-catalyzed asymmetric conjugate addition reactions, giving the corresponding addition products with higher enantioselectivity than other chiral dienes.

引用

页码：4387 / 4389

页数：3

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