Premium
Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines
Author(s) -
Moragas Toni,
Liffey Ryan M.,
Regentová Dominika,
Ward JonPaul S.,
Dutton Justine,
Lewis William,
Churcher Ian,
Walton Lesley,
Souto José A.,
Stockman Robert A.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201604188
Subject(s) - aziridine , chemistry , sigmatropic reaction , combinatorial chemistry , enantioselective synthesis , stereochemistry , organic chemistry , ring (chemistry) , catalysis
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.