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Borane‐Catalyzed Chemoselective and Enantioselective Reduction of 2‐Vinyl‐Substituted Pyridines
Author(s) -
Tian JunJie,
Yang ZhaoYing,
Liang XinShen,
Liu Ning,
Hu ChenYu,
Tu XianShuang,
Li Xiang,
Wang XiaoChen
Publication year - 2020
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.202007352
Subject(s) - hydroboration , enantioselective synthesis , chemistry , catalysis , borane , combinatorial chemistry , organic chemistry , transfer hydrogenation , bicyclic molecule , reagent , amide , ruthenium
Herein, we report that highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been achieved for the first time. The reaction, which uses chiral spiro‐bicyclic bisboranes as catalysts and HBpin and an acidic amide as reducing reagents, proceeds through a cascade process involving 1,4‐hydroboration followed by transfer hydrogenation of a dihydropyridine intermediate. The retained double bond in the reduction products permits their conversion to natural products and other useful heterocyclic compounds by simple transformations.