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

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

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 develo...

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Bibliographic Details
Main Authors: Moragas, Toni, Liffey, Ryan M., Regentova, Dominika, Ward, Jon-Paul, Dutton, Justine, Lewis, William, Churcher, Ian, Walton, Lesley, Souto, J.A., Stockman, Robert A.
Format: Article
Published: Wiley-VCH Verlag 2016
Online Access:https://eprints.nottingham.ac.uk/42559/
Description
Summary: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.

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