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.

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.

Citation

Moragas, T., Liffey, R. M., Regentova, D., Ward, J.-P., Dutton, J., Lewis, W., Churcher, I., Walton, L., Souto, J., & 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

• 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.
• Contract Date: May 9, 2017