Enantioselective synthesis of syn-2-amino-1,3-diols via organocatalytic sequential oxa-Michael/alpha-amination reactions of alpha,beta-unsaturated aldehydes

摘要

A general and efficient method for the enantioselective synthesis of syn-2-amino-1,3-diols is reported. It involves the methodology of secondary amine-catalyzed one-pot sequential oxa-Michael/alpha-amination reactions of alpha,beta-unsaturated aldehydes. This method has also been successfully applied to highly efficient total syntheses of (+)-safingol and D-threo-clavaminol H with excellent stereoselectivities. (C) 2016 Elsevier Ltd. All rights reserved.