Issue 15, 2018

C–H functionalization enabled stereoselective Ugi-azide reaction to α-tetrazolyl alicyclic amines

Abstract

An unprecedented stereoselective C(sp3)–H functionalization enabled Ugi-azide (CH-Ugi-azide) reaction is reported. This novel reaction produces α-tetrazolyl N-heterocycles directly from N-heterocycles without involving pre-functionalization/pre-oxidation steps. Importantly, the stereoselective reaction involving chiral amines or chiral isocyanides allowed the expeditious syntheses of nucleoside analogs and α-tetrazolyl pyrrolidine in enantioenriched form.

Graphical abstract: C–H functionalization enabled stereoselective Ugi-azide reaction to α-tetrazolyl alicyclic amines

Supplementary files

Article information

Article type
Communication
Submitted
17 May 2018
Accepted
09 Jul 2018
First published
09 Jul 2018

Green Chem., 2018,20, 3463-3467

C–H functionalization enabled stereoselective Ugi-azide reaction to α-tetrazolyl alicyclic amines

S. Haldar, S. Saha, S. Mandal and C. K. Jana, Green Chem., 2018, 20, 3463 DOI: 10.1039/C8GC01544A

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