Issue 34, 2015

Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction

Abstract

A simple and efficient synthetic route to substituted N-sulfinyl and N-sulfonyl azetidines is described involving imino-aldol reaction of ester enolates with racemic and non-racemic aldimines for obtaining β-amino esters as a key step. These β-amino esters on subsequent reduction followed by TsCl/KOH mediated cyclization produced the corresponding racemic and non-racemic azetidines with high yield and stereoselectivity.

Graphical abstract: Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction

Supplementary files

Article information

Article type
Paper
Submitted
07 Jun 2015
Accepted
20 Jul 2015
First published
20 Jul 2015
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2015,13, 9042-9049

Author version available

Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction

M. K. Ghorai, S. Das, K. Das and A. Kumar, Org. Biomol. Chem., 2015, 13, 9042 DOI: 10.1039/C5OB01140J

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