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Synthesis of N-p-Toluenesulphonyl-2-alkenyl aziridines by regioselective aziridination of 1,3-dienes

Lookup NU author(s): Dr Julian Knight

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Abstract

© 1995 Georg Thieme Verlag. All rights reserved. The regioselective copper catalysed aziridination of 1,3-dienes using PhI=NTs is reported. For unsymmetrical dienes, the major product is that resulting from reaction of the more electron rich double bond. When the two double bonds are electronically similar, steric hindrance governs the selectivity. In some cases rearrangement of the vinyl aziridine to the corresponding 3-pyrroline was observed. The reaction of 1,3-cyclooctadiene gave the 3-pyrroline (5) exclusively.

Publication metadata

Author(s): Knight JG, Muldowney MP

Publication type: Article

Publication status: Published

Journal: Synlett

Year: 1995

Volume: 1995

Issue: 9

Pages: 949-951

Print publication date: 01/09/1995

ISSN (print): 0936-5214

ISSN (electronic): 1437-2096

Publisher: Georg Thieme Verlag

URL: https://doi.org/10.1055/s-1995-5128

DOI: 10.1055/s-1995-5128

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