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Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reaction†‡
Manas K. Ghorai,Subhomoy Das,Kalpataru Das,Amit Kumar
Organic & Biomolecular Chemistry Pub Date : 07/20/2015 00:00:00 , DOI:10.1039/C5OB01140J
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
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