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

Chiral triazolium- and imidazolium-derived N-heterocyclic carbene catalysts promote the direct annulation of α,β-unsaturated aldehydes and achiral α-hydroxy enones to afford cyclopentane-fused lactones with high enantioselectivity. Remarkably, otherwise structurally identical imidazolium and triazol...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2009-02, Vol.11 (3), p.677-680
Main Authors: Kaeobamrung, Juthanat, Bode, Jeffrey W
Format: Article
Language:English
Subjects:
Catalysis
Cyclization
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Imidazoles - chemistry
Molecular Structure
Stereoisomerism
Triazoles - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Chiral triazolium- and imidazolium-derived N-heterocyclic carbene catalysts promote the direct annulation of α,β-unsaturated aldehydes and achiral α-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol802739d