Stereodivergency of triazolium and imidazolium-derived NHCs for catalytic, enantioselective cyclopentane synthesis.

ABSTRACT: 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.

SUBMITTER: Kaeobamrung J 

PROVIDER: S-EPMC2664100 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature