Angewandte Chemie - International Edition p. 7920 - 7926 (2021)
Update date:2022-08-03
Topics:
Annapureddy, Rajasekar Reddy
Burg, Finn
Gramüller, Johannes
Golub, Tino P.
Merten, Christian
Huber, Stefan M.
Bach, Thorsten
An enantioselective sulfimidation of 3-thiosubstituted 2-quinolones and 2-pyridones was achieved with a stoichiometric nitrene source (PhI=NNs) and a silver-based catalyst system. Key to the success of the reaction is the use of a chiral phenanthroline ligand with a hydrogen bonding site. The enantioselectivity does not depend on the size of the two substituents at the sulfur atom but only on the binding properties of the heterocyclic lactams. A total of 21 chiral sulfimides were obtained in high yields (44–99 %) and with significant enantiomeric excess (70–99 % ee). The sulfimidation proceeds with high site-selectivity and can also be employed for the kinetic resolution of chiral sulfoxides. Mechanistic evidence suggests the intermediacy of a heteroleptic silver complex, in which the silver atom is bound to one molecule of the chiral ligand and one molecule of an achiral 1,10-phenanthroline. Support for the suggested reaction course was obtained by ESI mass spectrometry, DFT calculations, and a Hammett analysis.
View MoreNanjing HuiBaiShi Biotechnology Co.,Ltd.
Contact:+86 (25)58745219
Address:No.606 Ningliu Road,LiuHe District.
Suzhou Credit International Trading Co., Ltd
Contact:+86-512-65398039
Address:Qingdeng, Hightech. District, Suzhou
Shanghai Kefu Chemical Co.,Ltd.
Contact:+86-21-34616196
Address:Room601-602, Xuhui Business Building, No.168, Yude Road, Shanghai
Shijiazhuang Sdyano Fine Chemical Co., Ltd
Contact:+86-311-89830448
Address:NO.48 Ta Nan Road,Yuhua District,Shijiazhuang,Hebei,China
Shandong Ailitong New Material Co.,Ltd
Contact:+86-536-3226266
Address:zhongjia village, putong town , qingzhou city,Shandong Province,China
Doi:10.1021/ja01645a016
(1954)Doi:10.1016/S0040-4039(00)84876-5
(1986)Doi:10.1248/cpb.35.4819
(1987)Doi:10.1016/j.tet.2008.07.111
(2008)Doi:10.1016/S0040-4039(00)84705-X
(1986)Doi:10.1002/hlca.19860690305
(1986)