Issue 24, 2017

Reaction of azides and enolisable aldehydes under the catalysis of organic bases and Cinchona based quaternary ammonium salts

Abstract

Herein we report a two-step sequence for the preparation of amides starting from azides and enolisable aldehydes. The reaction proceeded via the formation of triazoline intermediates that were converted into amides via Lewis acid catalysis. Preliminary studies on the preparation of triazolines under chiral phase transfer catalysis are also presented, demonstrating that enantioenriched amides could be prepared from achiral aldehydes in moderate to low enantioselectivity.

Graphical abstract: Reaction of azides and enolisable aldehydes under the catalysis of organic bases and Cinchona based quaternary ammonium salts

Supplementary files

Article information

Article type
Paper
Submitted
30 Mar 2017
Accepted
28 May 2017
First published
30 May 2017

Org. Biomol. Chem., 2017,15, 5227-5235

Reaction of azides and enolisable aldehydes under the catalysis of organic bases and Cinchona based quaternary ammonium salts

D. Destro, S. Sanchez, M. Cortigiani and M. F. A. Adamo, Org. Biomol. Chem., 2017, 15, 5227 DOI: 10.1039/C7OB00799J

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