Sigmatropic rearrangement of vinyl aziridines: expedient synthesis of cyclic sulfoximines from chiral sulfiniminesTools Moragas, Toni, Liffey, Ryan M., Regentova, Dominika, Ward, Jon-Paul, Dutton, Justine, Lewis, William, Churcher, Ian, Walton, Lesley, 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 Full text not available from this repository.AbstractA 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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