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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 20
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Original Articles

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

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Pages 2936-2942 | Received 05 Dec 2013, Published online: 08 Aug 2014
 

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

ACKNOWLEDGMENT

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

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