Reversal Diastereoselectivity Between the Organomagnesium and Organolithium Reagents on Chiral N-Tert-Butylsulfinylaldimines for the Preparation of Chiral Amines

Abstract

The asymmetric synthesis of both the enantiomer of chiral amines from the single chiral source of N-tert-butylsulfinylaldimines (3) by simply changing the organometallic reagents through diastereoselective addition. An efficient enantioselective synthesis of chiral amines including (S)-3-methyl-1-(2-piperidin-1-yl-phenyl)butyl amine (6a), a key intermediate to prepare antidiabetic drug repaglinide (1), is reported.

GRAPHICAL ABSTRACT

Keywords:

• 1-(2-Bromophenyl)piperidine
• isobutyraldehyde
• isovaleraldehyde
• n-butyraldehyde
• n-propionaldehyde
• S(–)-tert-butanesulfinamide
• titanium tetraethoxide

ACKNOWLEDGMENT

The authors greatly acknowledge Mr. Venkat Jasti, CEO, Suven Life Sciences Ltd., Hyderabad, for providing excellent facilities to carry out this work.