Organocatalytic sequential α-amination/Corey-Chaykovsky reaction of aldehydes: A high yield synthesis of 4-hydroxypyrazolidine derivatives

Abstract

A tandem reaction of in situ generated α-amino aldehydes with dimethyloxosulfonium methylide under Corey-Chaykovsky reaction conditions proceeds efficiently to give 4-hydroxypyrazolidine derivatives in high yields with excellent enantio- and diastereoselectivities. This organocatalytic sequential method provides for the efficient synthesis of anti-1,2- aminoalcohols, structural subunits present in several bioactive molecules as well. © 2012 American Chemical Society.