Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines. (13th July 2016)

• Record Type: Journal Article
• Authors: Moragas, Toni; Liffey, Ryan M.; Regentová, Dominika; Ward, Jon‐Paul S.; Dutton, Justine; Lewis, William; Churcher, Ian; Walton, Lesley; Souto, José A.; Stockman, Robert A.
• Is Part Of: Angewandte Chemie. Volume 128:Number 34(2016)
• Page Start: 10201
• Page End: 10205
• Publication Date: 2016-07-13
• Subjects: Heterocyclen -- Kleinringverbindungen -- Schwefel -- Synthesemethoden -- Umlagerungen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201604188
• Languages: English
• ISSNs: 0044-8249

Abstract

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, and tolerates a wide substrate scope. A one‐pot process starting directly from sulfinimines provides 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.