Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines |
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| Authors: | Dr Toni Moragas Ryan M Liffey Dr Dominika Regentová Jon‐Paul S Ward Justine Dutton Dr William Lewis Prof Ian Churcher Dr Lesley Walton Dr José A Souto Prof Robert A Stockman |
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| Institution: | 1. School of Chemistry, University of Nottingham, Nottingham, UK;2. GlaxoSmithKline Medicines Research Centre, Stevenage, UK;3. Lilly, UK, Windlesham, UK;4. Departamento de Química Orgánica, Universidade de Vigo, Vigo, Spain |
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| 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. |
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| Keywords: | heterocycles rearrangements small ring compounds sulfur synthetic methods |
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