title: Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines.
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.
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
authors.forename: Toni
authors.initials: T
authors.lastname: Moragas
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
authors.forename: Ryan M
authors.initials: RM
authors.lastname: Liffey
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
authors.forename: Dominika
authors.initials: D
authors.lastname: Regentová
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
authors.forename: Jon-Paul S
authors.initials: JP
authors.lastname: Ward
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
authors.forename: Justine
authors.initials: J
authors.lastname: Dutton
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.
authors.forename: William
authors.initials: W
authors.lastname: Lewis
authors.affiliation: GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, SG1 2NY, UK.
authors.forename: Ian
authors.initials: I
authors.lastname: Churcher
authors.affiliation: Lilly, UK, Erl Wood Manor, Windlesham, GU20 6PH, UK.
authors.forename: Lesley
authors.initials: L
authors.lastname: Walton
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK.|Departamento de Química Orgánica, Universidade de Vigo, 36310, Vigo, Spain.
authors.forename: José A
authors.initials: JA
authors.lastname: Souto
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK. robert.stockman@nottingham.ac.uk.
authors.forename: Robert A
authors.identifier: 0000-0002-7915-340X
authors.initials: RA
authors.lastname: Stockman
keywords: heterocycles; rearrangements; small ring compounds; sulfur; synthetic methods