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 International Edition Vol. 59; no. 42; pp. 18452 - 18456
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 12.10.2020
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
asymmetric catalysis
boron
Catalysts
Chemical reduction
Chemistry
Chemistry, Multidisciplinary
Dihydropyridine
Enantiomers
heterocycles
Heterocyclic compounds
Hydroboration
Natural products
Physical Sciences
pyridine
Pyridines
Reagents
reduction
Science & Technology
Substitutes
HYDROBORATION
MECHANISM
METAL-FREE HYDROGENATIONS
IMINES
pyridine
FRUSTRATED LEWIS PAIRS
asymmetric catalysis
MULTIPLE STEREOGENIC CENTERS
heterocycles
ASYMMETRIC HYDROGENATION
HYDROSILATION
reduction
boron
DERIVATIVES
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Abstract 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.
AbstractList 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.
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.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.
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.
Author Liu, Ning
Tian, Jun‐Jie
Hu, Chen‐Yu
Yang, Zhao‐Ying
Tu, Xian‐Shuang
Liang, Xin‐Shen
Li, Xiang
Wang, Xiao‐Chen
Author_xml – sequence: 1
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  surname: Tian
  fullname: Tian, Jun‐Jie
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  givenname: Zhao‐Ying
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  fullname: Yang, Zhao‐Ying
  organization: Nankai University
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  givenname: Xin‐Shen
  surname: Liang
  fullname: Liang, Xin‐Shen
  organization: Nankai University
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  surname: Liu
  fullname: Liu, Ning
  organization: Nankai University
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  surname: Hu
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  givenname: Xian‐Shuang
  surname: Tu
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  orcidid: 0000-0001-5863-0804
  surname: Wang
  fullname: Wang, Xiao‐Chen
  email: xcwang@nankai.edu.cn
  organization: Nankai University
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Issue 42
Keywords HYDROBORATION
MECHANISM
METAL-FREE HYDROGENATIONS
IMINES
pyridine
FRUSTRATED LEWIS PAIRS
asymmetric catalysis
MULTIPLE STEREOGENIC CENTERS
heterocycles
ASYMMETRIC HYDROGENATION
HYDROSILATION
reduction
boron
DERIVATIVES
Language English
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Snippet Herein, we report that highly chemoselective and enantioselective reduction of 2‐vinyl‐substituted pyridines has been achieved for the first time. The...
Herein, we report that highly chemoselective and enantioselective reduction of 2-vinyl-substituted pyridines has been achieved for the first time. The...
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SubjectTerms asymmetric catalysis
boron
Catalysts
Chemical reduction
Chemistry
Chemistry, Multidisciplinary
Dihydropyridine
Enantiomers
heterocycles
Heterocyclic compounds
Hydroboration
Natural products
Physical Sciences
pyridine
Pyridines
Reagents
reduction
Science & Technology
Substitutes
Title Borane‐Catalyzed Chemoselective and Enantioselective Reduction of 2‐Vinyl‐Substituted Pyridines
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202007352
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https://www.ncbi.nlm.nih.gov/pubmed/32640060
https://www.proquest.com/docview/2448266837
https://www.proquest.com/docview/2422006962
Volume 59
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