Stereoselective synthesis of activated 2-arylazetidines via imino-aldol reactionDedicated to Prof. Tarun Kumar Sarkar on his 67th birthday.Electronic supplementary information (ESI) available: Copies of 1H, and 13C NMR spectra and HPLC chromatogram. See DOI: 10.1039/c5ob01140j

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/...

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Bibliographic Details
Main Authors: Ghorai, Manas K, Das, Subhomoy, Das, Kalpataru, Kumar, Amit
Format: Article
Language:English
Online Access:Get full text
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Summary: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. A highly stereoselective synthesis of N -sulfinyl and N -sulfonyl azetidines have been developed involving imino-aldol reaction of ester enolates with aldimines.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob01140j