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Enantioselective Copper‐Catalyzed Three‐Component Carboboronation of Allenes: Access to Functionalized Dibenzo [ b,f ][1,4]oxazepine Derivatives
Author(s) -
Deng Hao,
Meng Ziwei,
Wang Sifan,
Zhang Zheming,
Zhang Yaqi,
Shangguan Yu,
Yang Fazhou,
Yuan Dekai,
Guo Hongchao,
Zhang Cheng
Publication year - 2019
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.201900503
Subject(s) - enantioselective synthesis , chemistry , ligand (biochemistry) , yield (engineering) , catalysis , copper , chiral ligand , medicinal chemistry , combinatorial chemistry , component (thermodynamics) , stereochemistry , organic chemistry , receptor , biochemistry , materials science , physics , metallurgy , thermodynamics
A copper‐catalyzed enantioselective three‐component difunctionalization of allenes with seven‐membered cyclic imines and bis(pinacolato)diboron (B 2 (Pin) 2 ) to approach functionalized dibenzo[ b,f ][1,4]oxazepine derivatives is developed. The chiral products are obtained in up to 81% yield, >20:1 dr, and 98% ee when either a chiral diphosphine ligand or a chiral ferrocenyl‐based P,N‐ligand is used. Furthermore, the reaction exhibits reversed diastereoselectivities when the chiral diphosphine ligand and the chiral P,N‐ligand are used respectively.