Angewandte Chemie - International Edition p. 5834 - 5838 (2017)
Update date:2022-08-03
Topics:
Manzano, Rubén
Datta, Swarup
Paton, Robert S.
Dixon, Darren J.
A silver(I) and amine co-catalyzed desymmetrization of 4-propargylamino cyclohexanones for the direct enantioselective synthesis of 2-azabicyclo[3.3.1]nonanes is described. Exploiting reactivity arising from dual activation of the pendant terminal alkyne by silver(I) and the ketone moiety through transient enamine formation, this synthetically relevant transformation is easy to perform, efficient and broad in scope. High enantioselectivity (up to 96 % ee) was achieved by exploiting a significant matching effect between the chirality of a cinchona alkaloid-derived aminophosphine ligand for the silver(I) salt and the 2-bis(aryl)methylpyrrolidine catalyst which was rationalized by DFT calculations. This allowed for the preparation of both enantiomers of the bicyclic product with near-identical stereocontrol.
View MoreHeliosense Biotechnologies, Inc.
Contact:+86-592-5667290
Address:Xiamen Torch Hi-tech Zone Venture Weiye Building S506
Xi'an HO-SHINE Bio-Technology Co., Ltd
Contact:+86 (29) 8248-5435/18292020086
Address:No.6 Shiyuan Road Xian City Shaanxi Province, 710048 China
Hubei Danao Pharmaceutical Co.,Ltd.
website:http://www.danaopharm.com
Contact:+86-719-5251167
Address:Fandan Road,Danjiangkou,Hubei
Contact:+86-577-65618087-605
Address:Room 402, Unit 4 Xinhu Bldg. Waitan Ruian City, Zhejiang China.
Jewim Pharmaceutical (Shandong) Co., Ltd
Contact:+8615621883869
Address:山东省泰安市高新技术产业开发区配天门大街西首
Doi:10.1016/j.tetlet.2009.07.060
(2009)Doi:10.1016/j.bmcl.2007.05.102
(2007)Doi:10.1021/ol071332c
(2007)Doi:10.1021/jo070750s
(2007)Doi:10.1016/j.bmcl.2008.10.056
(2008)Doi:10.1016/S0040-4020(01)96892-9
(1984)