Sigmatropic rearrangement of vinyl aziridines: expedient synthesis of cyclic sulfoximines from chiral sulfinimines

Moragas, Toni and Liffey, Ryan M. and Regentova, Dominika and Ward, Jon-Paul and Dutton, Justine and Lewis, William and Churcher, Ian and Walton, Lesley and Souto, J.A. and Stockman, Robert A. (2016) Sigmatropic rearrangement of vinyl aziridines: expedient synthesis of cyclic sulfoximines from chiral sulfinimines. Angewandte Chemie International Edition, 55 (34). pp. 10047-10051. ISSN 1521-3773

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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.

Item Type: Article
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.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.
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: 10.1002/anie.201604188
Depositing User: Smith, Ruth
Date Deposited: 09 May 2017 14:06
Last Modified: 13 Oct 2017 00:47
URI: http://eprints.nottingham.ac.uk/id/eprint/42559

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