Chiral Binaphthol-Catalyzed Enantioselective Conjugate Addition of Alkenyl and Arylboronic Acids to α,β-Unsaturated Cyclic <i>N</i>-Sulfonyl Ketimines

The chiral binaphthol-catalyzed enantioselective conjugate addition of alkenylboronic acids and heteroarylboronic acids to cyclic <i>N</i>-sulfonyl ketimines is reported, providing the 1,4-addition products in high yields and moderate to excellent enantioselectivities (up to >99% ee). This mild, scalable catalytic system exhibits high efficiency and broad substrate scopes. Additionally, arylboronic acids were viable nucleophiles under more forcing conditions.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-09-03
DOI
https://doi.org/10.1021/acs.joc.4c01269
Citations
2
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
0.50

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article

Chiral Binaphthol-Catalyzed Enantioselective Conjugate Addition of Alkenyl and Arylboronic Acids to α,β-Unsaturated Cyclic N-Sulfonyl Ketimines

Yang-Ling Wang, Junbiao Chang, Guo-Li Chai, Yajing Hou
2 citations
The Journal of Organic Chemistry
Asymmetric Synthesis and Catalysis
0.50
article

Chiral Binaphthol-Catalyzed Enantioselective Conjugate Addition of Alkenyl and Arylboronic Acids to α,β-Unsaturated Cyclic N-Sulfonyl Ketimines

Yang-Ling Wang, Junbiao Chang, Guo-Li Chai, Yajing Hou
article en
2 citations

Abstract

The chiral binaphthol-catalyzed enantioselective conjugate addition of alkenylboronic acids and heteroarylboronic acids to cyclic <i>N</i>-sulfonyl ketimines is reported, providing the 1,4-addition products in high yields and moderate to excellent enantioselectivities (up to >99% ee). This mild, scalable catalytic system exhibits high efficiency and broad substrate scopes. Additionally, arylboronic acids were viable nucleophiles under more forcing conditions.

The Journal of Organic ChemistryVol. 89(18)
Henan Normal University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Henan Province, Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Central Plains Scholars and Scientists Studio Fund
Openalex Percentile: Top 40%
Asymmetric Synthesis and Catalysis
0.50
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