Premium
Bifunctional Borane Catalysis of a Hydride Transfer/Enantioselective [2+2] Cycloaddition Cascade
Author(s) -
Zhang Ming,
Wang XiaoChen
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202106168
Subject(s) - enantioselective synthesis , bifunctional , cycloaddition , hydride , catalysis , substrate (aquarium) , chemistry , borane , combinatorial chemistry , cascade , transfer hydrogenation , cascade reaction , organic chemistry , oceanography , ruthenium , geology , hydrogen , chromatography
Herein, we present a mild and efficient method for synthesizing enantioenriched tetrahydroquinoline‐fused cyclobutenes through a cascade reaction between 1,2‐dihydroquinolines and alkynones with catalysis by chiral spiro‐bicyclic bisboranes. The bisboranes served two functions: first they catalyzed a hydride transfer to convert the 1,2‐dihydroquinoline substrate to a 1,4‐dihydroquinoline, and then they activated the alkynone substrate for an enantioselective [2+2] cycloaddition reaction with the 1,4‐dihydroquinoline generated in situ.