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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.

Authors

Toni Moragas

Ryan M. Liffey

Dominika Regentova

Jon-Paul Ward

Justine Dutton

William Lewis

Ian Churcher

Lesley Walton

J.A. Souto



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
Publication Date Aug 16, 2016
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
APA6 Citation Moragas, T., Liffey, R. M., Regentova, D., Ward, J., Dutton, J., Lewis, W., …Stockman, R. A. (2016). Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines. Angewandte Chemie International Edition, 55(34), 10047-10051. https://doi.org/10.1002/anie.201604188
DOI https://doi.org/10.1002/anie.201604188
Publisher URL https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201604188
Copyright Statement Copyright information regarding this work can be found at the following address: http://eprints.nottingh.../end_user_agreement.pdf
Additional Information This is the peer reviewed version of the following article: T. Moragas, R. M. Liffey, D. Regentov√°, 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.wi...nie.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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Copyright Statement
Copyright information regarding this work can be found at the following address: http://eprints.nottingham.ac.uk/end_user_agreement.pdf





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