ACS Catalysis p. 1308 - 1315 (2016)
Update date:2022-08-11
Topics:
Ogasawara, Masamichi
Arae, Sachie
Watanabe, Susumu
Nakajima, Kiyohiko
Takahashi, Tamotsu
Highly enantioselective kinetic resolution of racemic planar-chiral metallocenylphosphine sulfides was realized by the molybdenum-catalyzed asymmetric ring-closing metathesis reaction with the krel values of up to 147. The enantiomerically enriched 1,4-but-2-enylene-bridged ferrocenylphosphine sulfides thus obtained could be purified to enantiomerically pure forms by simple recrystallization from hot methanol, and subsequent reduction of the phosphine sulfides provided the corresponding planar-chiral phosphines with retention of the enantiomeric homogeneity. This is a rare example of preparing planar-chiral ferrocenylphosphines by catalytic asymmetric reactions. The single-enantiomer planar-chiral ferrocenylphosphines were applied as chiral ligands in the rhodium-catalyzed asymmetric 1,4-addition reaction (the Hayashi-Miyaura conjugate addition reaction) of phenylboronic acid to 2-cyclohexenone to show excellent enantioselectivity and high yields. The NMR studies clarified that the butenylene-bridged ferrocenylphosphine coordinated to a rhodium(I) cation in a monodentate fashion and an interaction of the bridging olefin moiety to the rhodium atom was not detected.
View MoreAnhui Redstar Pharmaceutical Corp., Ltd
Contact:+86-563-5120837
Address:Jingxian Industrial Development Zone, Anhui , China
Contact:+86-25-83719363
Address:106-7 Chunnan Rd, Chunxi Town, Gaochun, Nanjing, China
Hunan Zhongqi Pharmaceutical Co., Ltd
website:http://www.hnzqzy.com
Contact:0730-8722288 13807308622
Address:Wanjiafan Road ,Yueyang Economic And Technological Development Zone ,Hunan,PRC
website:http://www.uvchemkleys.com
Contact:+86 21 3868 0172
Address:RM-1203, Ziguang Building, #341 Shangcheng Road, Pudong Dist, Shanghai
Chongqing Werlchem Fine Chemical Co. Ltd
Contact:+86-23-67521957
Address:NO.15,Fortune Road,Yubei District,401121,Chongqing,China
Doi:10.1002/cctc.201200329
(2013)Doi:10.1039/c9tc05996b
(2019)Doi:10.1016/j.crci.2012.06.010
(2012)Doi:10.1007/BF02766093
()Doi:10.1080/15257770.2010.537291
(2011)Doi:10.1016/0022-328X(91)80240-K
(1991)