Lewis Acid-Catalyzed Diastereoselective Synthesis of Multisubstituted N-Acylaziridine-2-carboxamides from 2 H-Azirines via Joullié-Ugi Three-Component Reaction

A ZnCl -catalyzed diastereoselective Joullié-Ugi three-component reaction from 2 H-azirines, isocyanides, and carboxylic acids was established. The protocol allows the preparation of highly and diversely functionalized N-acylaziridine-2-carboxamide derivatives in up to 82% isolated yields. Moreover,...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-04, Vol.83 (7), p.3570-3581
Main Authors: Angyal, Anikó, Demjén, András, Wéber, Edit, Kovács, Anita K, Wölfling, János, Puskás, László G, Kanizsai, Iván
Format: Article
Language:English
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Summary:A ZnCl -catalyzed diastereoselective Joullié-Ugi three-component reaction from 2 H-azirines, isocyanides, and carboxylic acids was established. The protocol allows the preparation of highly and diversely functionalized N-acylaziridine-2-carboxamide derivatives in up to 82% isolated yields. Moreover, the applicability of N-acylaziridines is demonstrated through a variety of transformations.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b03189