Journal of Organic Chemistry p. 2420 - 2431 (2016)
Update date:2022-08-04
Topics:
Madhusudhan Reddy
Ko, Chi-Ting
Hsieh, Kai-Hong
Lee, Chia-Jui
Das, Utpal
Lin, Wenwei
A cinchona-alkaloid-derived chiral primary-amine-catalyzed enantioselective method for the synthesis of the thermodynamically less stable indanedione-fused 2,6-trans-disubstituted spirocyclohexanones is demonstrated. Both the enantiomeric forms of the trans isomer are obtained in excellent yields and enantioselectivities. Furthermore, one of the enantiopure trans-spiranes bearing an additional α-substitution on the cyclohexanone ring was then epimerized into its thermodynamically stable cis counterpart, with little loss of enantioselectivity to demonstrate the feasibility of such a transformation. Mechanistic investigations revealed two competing pathways, a concerted Diels-Alder reaction and a stepwise Michael addition, for the formation of corresponding products.
View MoreAllyChem Co., Ltd., Dalian, China(BBChem)
Contact:+86-411-62313318/62313328
Address:No.5 of Jinbin Road, Jinzhou New District, Dalian City, Liaoning Province, P.R.China
Zhonghao (dalian) Research and Design Institute of Chemical Industry Co., Ltd
Contact:+86 411 84674606
Address:201, Huangpu Road , Shahekou District, Dalian ,116023-China
Shanghai Send Pharmaceutical Technology Co., Ltd.
website:http://www.shsendpharma.com
Contact:021-58088081, +8613585868794
Address::Room A601, Building 1,NO. 800 Qingdai Road Pudong District Shanghai,China
Jiangxi Hessence Chemicals Co., Ltd.
Contact:+86 796 3511924
Address:Chengxi Industrial Park, Jishui County, Jiangxi Province 331600 China.
zhenjiang runjing high purity chemical co ltd
Contact:+86-511-83361155
Address:No.8.haixi road,international chemical park
Doi:10.1055/s-1999-2969
(1999)Doi:10.1016/S0968-0896(02)00009-3
(2002)Doi:10.1021/jo991307n
(2000)Doi:10.1016/S0040-4020(99)00914-X
(1999)Doi:10.1016/j.ejmech.2021.113327
(2021)Doi:10.1016/S0040-4039(01)02203-1
(2002)