Aerobic oxidation and EATA-based highly enantioselective synthesis of lamenallenic acid

Abstract

By utilizing the recently developed EATA (enantioselective allenylation of terminal alkynes) reaction and the aerobic oxidation of alcohols, lamenallenic acid, a naturally occurring axially chiral allene, has been synthesized with a high ee value and E/Z selectivity from methyl 5-hexynoate and (E)-10-dodecenal, which could be prepared easily from 1-decyne and 1-pentyne, respectively, with (S)-α,α-dimethylprolinol as the chiral source.