Issue 37, 2006

Ring-expansion of tertiary cyclic α-vinylamines by tandem conjugate addition to (p-toluenesulfonyl)ethyne and formal 3-aza-Cope rearrangement

Abstract

A novel ring-expansion protocol is based on the conjugate additions of cyclic α-vinylamines to (p-toluenesulfonyl)ethyne, followed by aza-Cope rearrangements of the resulting zwitterions, to afford medium and large-ring cyclic amines under remarkably mild conditions.

Graphical abstract: Ring-expansion of tertiary cyclic α-vinylamines by tandem conjugate addition to (p-toluenesulfonyl)ethyne and formal 3-aza-Cope rearrangement

Supplementary files

Article information

Article type
Communication
Submitted
31 May 2006
Accepted
30 Jun 2006
First published
07 Aug 2006

Chem. Commun., 2006, 3903-3905

Ring-expansion of tertiary cyclic α-vinylamines by tandem conjugate addition to (p-toluenesulfonyl)ethyne and formal 3-aza-Cope rearrangement

M. H. Weston, K. Nakajima, M. Parvez and T. G. Back, Chem. Commun., 2006, 3903 DOI: 10.1039/B607713G

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