Enantioselective Synthesis of syn-2-Amino-1,3-diols via Organocatalytic Sequential oxa-Michael/α-Amination Reactions of α,β-Unsaturated Aldehydes.

Abstract 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/α-amination reactions of α,β-unsaturated aldehydes. This method has also been successfully applied to highly efficient total syntheses of (+)-safingol and d -threo-clavaminol H with excellent stereoselectivities.