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Calcium‐Catalyzed Synthesis of 1,2‐Disubstituted 3‐Benzazepines
Author(s) -
Damsen Helena,
Niggemann Meike
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501106
Subject(s) - benzazepines , chemistry , enantiopure drug , benzazepine , intramolecular force , combinatorial chemistry , stereoselectivity , alkylation , stereochemistry , reagent , catalysis , stereoisomerism , enantioselective synthesis , organic chemistry
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.