Addition of the Lithium Anion of Diphenylmethanol Methyl/Methoxymethyl Ether to Nonracemic Sulfinimines: Two-Step Asymmetric Synthesis of Diphenylprolinol Methyl Ether and Chiral (Diphenylmethoxymethyl)amines.

Abstract

Addition of the lithium anion generated from diphenylmethanol methyl and methoxymethyl ether to nonracemic sulfinimines afforded the corresponding addition products in excellent diastereoselctivity and yields. Deprotection of the MOM as well as sulfinyl groups rendered the enantiopure (diphenylhydroxymethyl)amines in excellent yields. The procedure was applied for a two-step synthesis of diphenylprolinol, a privileged ligand in asymmetric catalysis.