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Organic letters

Iridium-catalyzed asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones: enantioselective total synthesis of (-)-mesembrine.


PMID 23210605

Abstract

A highly efficient asymmetric hydrogenation of α-substituted α,β-unsaturated acyclic ketones catalyzed by chiral spiro iridium complexes for the preparation of chiral 2-substituted allylic alcohols has been developed (ee up to 99.7%). This method provides a concise route to (-)-mesembrine (34% yield, 12 steps).