Bifunctional Borane Catalysis of a Hydride Transfer/Enantioselective [2+2] Cycloaddition Cascade | Zendy

Zhang Ming | Zendy; Wang XiaoChen | Zendy

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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.

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