ChemInform Abstract: Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines

Autor:	José A. Souto, Jon-Paul S. Ward, Lesley Walton, Justine Dutton, Ryan M. Liffey, William Lewis, Toni Moragas, Robert A. Stockman, Dominika Regentova, Ian Churcher
Rok vydání:	2016
Předmět:	Formal synthesis chemistry.chemical_compound Chemistry General Medicine Pyrroline Sigmatropic reaction Aziridine Trachelanthamidine Combinatorial chemistry
Zdroj:	ChemInform. 47
ISSN:	0931-7597
DOI:	10.1002/chin.201651183
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::bf16c2d1556fe4485111946f5a43fbca https://doi.org/10.1002/chin.201651183 Zobrazit plný text záznamu Plný text