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Direct and Enantioselective Synthesis of N−H‐Free 1,5‐Benzodiazepin‐2‐ones by an N‐Heterocyclic Carbene Catalyzed [3+4] Annulation Reaction
Author(s) -
Fang Chao,
Cao Jing,
Sun Kewen,
Zhu Jindong,
Lu Tao,
Du Ding
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201705050
Subject(s) - annulation , enantioselective synthesis , carbene , catalysis , combinatorial chemistry , aryl , chemistry , stereochemistry , organic chemistry , alkyl
An NHC‐catalyzed formal [3+4] annulation of α,β‐unsaturated acylazoliums with protecting‐group‐free aryl 1,2‐diamines was developed for a direct and highly enantioselective synthesis of 4‐aryl N−H‐free 1,5‐benzodiazepin‐2‐ones. This methodology offers an efficient and rapid access to a wide range of enantioenriched target compounds from easily accessible starting materials. The protocol is also scalable and the desired products can easily undergo subsequent N‐functionalization to afford diverse N‐substituted derivatives. Additionally, a mechanism was proposed to explain the high enantioselectivity in this process.