Recent advances in the use of chiral aldimines in asymmetric synthesis

Abstract

Chiral N-(tert-butyl)sulfinyl aldimines easily prepared from commercially available compounds have been used as starting materials for the following processes: (i) hydrogen transfer, (ii) addition of zincates, (iii) In-promoted allylation, and (iv) addition of zinc enolates. In all cases, the final desulfinylation to yield the expected chiral α-substituted primary amines was easily performed with hydrochloric acid in an organic solvent. This methodology has been successfully applied to the preparation of chiral natural products such as alkaloids and amino acids.