European Journal of Organic Chemistry p. 7880 - 7883 (2015)
Update date:2022-08-10
Topics:
Damsen, Helena
Niggemann, Meike
A short and highly stereoselective chiral pool synthesis of tetrahydro-3-benzazepines as potential drug molecules is described, using simple enantiopure amino acids as the chiral building blocks. Intramolecular Friedel-Crafts alkylation towards seven-membered rings was achieved with high diastereoselectivity for the first time and accomplished by a biocompatible calcium catalyst. The simple and cost efficient approach allows for the variation of all substituents in the 3-benzazepine by a change of the substitution pattern in one or more of the reagents, while leaving the general synthetic route unchanged. Furthermore, assignment of the absolute configuration of the 3-benzazepine derivative is straightforward, based on the amino acid building block employed. A new stereoselective chiral pool synthesis of 1,2-disubstituted 3-benzazepines was developed, using enantiopure amino acids as chiral building blocks. The key step is based on the first diastereoselective Friedel-Crafts cyclization towards this pharmacologically highly interesting compound class and accomplished by a biocompatible calcium catalyst. The modular concept allows for variation of all substituents, leaving the general synthetic route unchanged.
View MoreZibo Jujin Chemical Industry Co., Ltd.(Dongming Jujin Chemical Industry Co., Ltd. )
Contact:+86-533-2975022
Address:No.99 Shanquan Road, Zhangdian District
Hangzhou Eastbiopharm Co.,Ltd.
Contact:+86-571-88931780
Address:Hangzhou,China
Jiangxi Dongxu Chemical Science & Technology Co.,Ltd
Contact:+86-791-86899381
Address:Nanchang, Jiangxi, China
HaiNan Periwinkle Pharmaceutical Co.,Ltd.
website:http://www.cchpharm.com/en/index.html
Contact:020-82208978
Address:Gongye road,Wuzhishan city,HaiNan province
Shandong Xinhua Pharmaceutical Co.,Ltd
website:http://www.xhzy.com
Contact:+86-533-2196801
Address:1 lutai road,zhangdian dis,Zibo City
Doi:10.1246/bcsj.47.2813
(1974)Doi:10.1021/jacs.5b10221
(2015)Doi:10.1016/j.orgel.2020.105726
(2020)Doi:10.1016/S0031-9422(00)90634-4
(1994)Doi:10.1039/c0gc00704h
(2011)Doi:10.1021/ja01480a028
(1961)