Chemistry - A European Journal p. 7846 - 7849 (2009)
Update date:2022-09-26
Topics:
Galzerano, Patrizia
Bencivenni, Giorgio
Pesciaioli, Fabio
Mazzanti, Andrea
Giannichi, Berardino
Sambri, Letizia
Bartoli, Giuseppe
Melchiorre, Paolo
The development of a new bifunctional chiral primary amine thiourea catalyst and its application in the first asymmetric conjugate addition of oxindoles to enales was described. The reaction between 3-methyl oxindole and cinnamaldehyde, a combination of simple and readily available starting materials that targets in organic synthesis, was selected. The poor catalytic performance and the very low selectivity observed suggest a critical role of the thiourea moiety during the steroselective C-C bond-forming step. It is also found that by using 50% of benzoic acid, the catalyst loading is reduced to 10%, while still maintaining high diastero and enantiocontrol, and significant reactivity. The best diasterocontrol is observed for enals that have a naphthyl β substituted and by using oxindole that has a benzyl substitute.
View MoreContact:+86-575-82733999 0575-82732999
Address:hangzhou gulf fine chemical zone,shangyu city,zhejiang province
WUHU HUAHAI BIOLOGY ENGINEERING CO LTD
Contact:+86-553-3836920
Address:7/F NO.82 LAODONG ROAD WUHU CHINA
Yancheng Creator Chemical Co., Ltd
Contact:0086-515-88710008 88710068 88710858 88710868
Address:No.21 Renming Road, Longgang Town, Yandu County,Yancheng City
Suzhou Jingye Medicine & Chemical Co., Ltd
website:http://www.jingyechem.cn
Contact:+86-512-66658588
Address:No. 88, Sanlian Street, Jinfeng Road, Suzhou New District, Jiangsu Province, P. R. China
Chongqing Changfeng Chemical Co., Ltd.
website:http://www.changfengchem.com
Contact:+86-23-67896333
Address:30th Floor, Longhu Ziduxingzuo Building A, 1st Branch,YuSong Rd., Yubei District, Chongqing, China
Doi:10.1007/s10593-009-0329-0
(2009)Doi:10.1016/0040-4039(91)80491-N
(1991)Doi:10.1021/ic502557w
(2015)Doi:10.1016/j.tet.2008.10.093
(2009)Doi:10.1016/j.tetlet.2009.09.088
(2009)Doi:10.1039/c39940002289
(1994)