Premium
Enantioselective Construction of the Biologically Significant Dibenzo[1,4]diazepine Scaffold via Organocatalytic Asymmetric Three‐Component Reactions
Author(s) -
Wang Yang,
Tu ManSu,
Shi Feng,
Tu ShuJiang
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400095
Subject(s) - chemistry , diazepine , enantioselective synthesis , catalysis , yield (engineering) , cyclohexane , combinatorial chemistry , component (thermodynamics) , scaffold , phosphoric acid , organocatalysis , organic chemistry , ring (chemistry) , medicine , physics , biomedical engineering , thermodynamics , materials science , metallurgy
The first catalytic asymmetric construction of the biologically important dibenzo[1,4]diazepine scaffold has been established via SPINOL‐derived chiral phosphoric acid‐catalyzed three‐component reactions of aldehydes, 1,2‐phenylenediamines and cyclohexane‐1,3‐diones, which afforded structurally complex and diverse dibenzo[1,4]diazepines in high yields and good enantioselectivities (up to 98% yield, 92:8 er ). This transformation also represents the first catalytic asymmetric version of this three‐component reaction and provides an easy access to structurally rigid seven‐membered chiral heterocycles.