Borane‐Catalyzed Chemoselective and Enantioselective Reduction of 2‐Vinyl‐Substituted Pyridines

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 pro...

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Published inAngewandte Chemie Vol. 132; no. 42; pp. 18610 - 18614
Main Authors Tian, Jun‐Jie, Yang, Zhao‐Ying, Liang, Xin‐Shen, Liu, Ning, Hu, Chen‐Yu, Tu, Xian‐Shuang, Li, Xiang, Wang, Xiao‐Chen
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 12.10.2020
Subjects
asymmetric catalysis
boron
Catalysts
Chemical reduction
Chemistry
Dihydropyridine
Enantiomers
heterocycles
Heterocyclic compounds
Hydroboration
Natural products
pyridine
Pyridines
Reagents
reduction
Substitutes
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Summary: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. A protocol for Lewis acid‐catalyzed highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been developed. The reactions were catalyzed by chiral spiro‐bicyclic bisboranes and occurred under mild reaction conditions with high turnover numbers.
Bibliography:These authors contributed equally to this work.
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content type line 14
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202007352