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One‐Pot Enantioselective Aziridination of Olefins Catalyzed by a Copper( I ) Complex of a Novel Diimine Ligand by Using PhI(OAc) 2 and Sulfonamide as Nitrene Precursors
Author(s) -
Wang Xisheng,
Ding Kuiling
Publication year - 2006
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200501109
Subject(s) - diimine , nitrene , sulfonamide , enantioselective synthesis , ligand (biochemistry) , catalysis , copper , chemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , stereochemistry , polymer chemistry , receptor , biochemistry
A novel chiral C 2 ‐symmetric 1,4‐diamine with multistereogenic centers at the backbone of the ligand has been synthesized from cheap natural product D ‐mannitol through multistep transformations. Its diimine derivative ( 3 a ) was found to be highly effective for the enantioselective control of the copper‐catalyzed asymmetric aziridination of olefin derivatives with PhINTs as the nitrene source, affording the corresponding N ‐sulfonylated azirindine derivatives in good to excellent yields with up to 99 % ee ( ee =enantiomeric excess). The catalyst system discovered in the present work was also extended to a one‐pot enantioselective aziridination by using sulfonamide/iodobenzene diacetate as the nitrene source. In this case, most reactions proceeded smoothly to give the corresponding products in moderate yields with good to excellent enantiomeric excesses (75–96 % ee ).