Iridium-catalyzed regioselective and enantioselective allylation of trimethylsiloxyfuran.

ABSTRACT: We report the regio- and enantioselective allylation of an ester enolate, trimethylsiloxyfuran. This enolate reacts at the 3-position with linear aromatic allylic carbonates or aliphatic allylic benzoates to form the branched substitution products in the presence of a metallacyclic iridium catalyst. This process provides access to synthetically important 3-substituted butenolides in enantioenriched form. Stoichiometric reactions of the allyliridium intermediate suggest that the trimethylsiloxyfuran is activated by the carboxylate leaving group.

SUBMITTER: Chen W 

PROVIDER: S-EPMC3487469 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature