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Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines

Moragas, Toni; Liffey, Ryan M.; Regentova, Dominika; Ward, Jon-Paul; Dutton, Justine; Lewis, William; Churcher, Ian; Walton, Lesley; Souto, J.A.; Stockman, Robert A.

Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines Thumbnail


Authors

Toni Moragas

Ryan M. Liffey

Dominika Regentova

Jon-Paul Ward

Justine Dutton

William Lewis

Ian Churcher

Lesley Walton

J.A. Souto

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ROBERT STOCKMAN robert.stockman@nottingham.ac.uk
Professor of Organic Chemistry



Abstract

A novel rearrangement of 2-vinyl aziridine 2-carboxylates to unusual chiral cyclic sulfoximines is described herein. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, displaying a wide substrate scope under mild conditions. Further development of a one-pot process directly from sulfinimines shows the synthetic applicability of this protocol, providing access to complex chiral sulfoximines in only two steps from commercially available aldehydes. A mechanistic hypothesis and synthetic application in the formal synthesis of trachelanthamidine by transformation of a cyclic sulfoximine into a pyrroline is also disclosed.

Journal Article Type Article
Acceptance Date Jun 13, 2016
Online Publication Date Jul 13, 2016
Publication Date Aug 16, 2016
Deposit Date May 9, 2017
Publicly Available Date May 9, 2017
Journal Angewandte Chemie International Edition
Print ISSN 1433-7851
Electronic ISSN 1521-3773
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 55
Issue 34
Pages 10047-10051
DOI https://doi.org/10.1002/anie.201604188
Keywords heterocycles, rearrangements, small ring compounds, sulfur, synthetic methods
Public URL https://nottingham-repository.worktribe.com/output/803797
Publisher URL https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201604188
Additional Information This is the peer reviewed version of the following article: T. Moragas, R. M. Liffey, D. Regentová, J.-P. S. Ward, J. Dutton, W. Lewis, I. Churcher, L. Walton, J. A. Souto, R. A. Stockman, Angew. Chem. Int. Ed. 2016, 55, 10047., which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/anie.201604188/abstract. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.

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