Umpolung of Michael acceptors catalyzed by N-heterocyclic carbenes.

ABSTRACT: N-Heterocyclic carbenes can catalyze beta-alkylations of a range of alpha,beta-unsaturated esters, amides, and nitriles that bear pendant leaving groups to form a variety of ring sizes. In this process, the nucleophilic catalyst transiently transforms the normally electrophilic beta carbon into a nucleophilic site through an unanticipated addition-tautomerization sequence.

SUBMITTER: Fischer C 

PROVIDER: S-EPMC2553003 | biostudies-literature | 2006 Feb

REPOSITORIES: biostudies-literature