Stereodivergency of Triazolium and Imidazolium-Derived NHCs for Catalytic, Enantioselective Cyclopentane Synthesis

被引：108

作者：

Kaeobamrung, Juthanat ^{[1
]}

Bode, Jeffrey W. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 03期

关键词：

INTRAMOLECULAR STETTER REACTION; DIELS-ALDER REACTIONS; N-HETEROCYCLIC CARBENES; GAMMA-BUTYROLACTONES; DIRECT ANNULATIONS; BETA-LACTONES; ENALS; GENERATION; ALDEHYDES;

D O I：

10.1021/ol802739d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral triazolium- and imidazolium-derived N-heterocyclic carbene catalysts promote the direct annulation of alpha,beta-unsaturated aldehydes and achiral alpha-hydroxy enones to afford cyclopentane-fused lactones with high enantioselectivity. Remarkably, otherwise structurally identical imidazolium and triazolium precatalysts afford different major products. These studies provide both an efficient entry to valuable chiral structures and a dramatic demonstration of stereodivergency of chiral imidazolium versus triazolium-derived N-heterocyclic carbene catalysts.

引用

页码：677 / 680

页数：4

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