Hydroxy Group-Assisted Cu-Catalyzed Asymmetric Conjugate Addition for the Creation of an All-Carbon Quaternary Center

Multinuclear Cu-catalyzed conjugate addition of Me3Al to α’-hydroxy enones was achieved in high to excellent enantioselectivity. In control experiments, we revealed that conjugate addition of Me3Al to β,β-disubstituted α’-hydroxy enones was an important contributor, even without ligands, which implies that the hydroxy moiety helps to facilitate the reaction. The corresponding products can be converted to various carbonyl compounds through oxidative cleavage of the C–C bond.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-05-18
DOI
https://doi.org/10.1021/acs.joc.6c00144
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Hydroxy Group-Assisted Cu-Catalyzed Asymmetric Conjugate Addition for the Creation of an All-Carbon Quaternary Center

Kohei Endo, Ken Yamanomoto, Y. Shiratori, Taiyo Yamamoto et al.
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Hydroxy Group-Assisted Cu-Catalyzed Asymmetric Conjugate Addition for the Creation of an All-Carbon Quaternary Center

Kohei Endo, Ken Yamanomoto, Y. Shiratori, Taiyo Yamamoto, Shogo Yamaguchi
article en

Abstract

Multinuclear Cu-catalyzed conjugate addition of Me3Al to α’-hydroxy enones was achieved in high to excellent enantioselectivity. In control experiments, we revealed that conjugate addition of Me3Al to β,β-disubstituted α’-hydroxy enones was an important contributor, even without ligands, which implies that the hydroxy moiety helps to facilitate the reaction. The corresponding products can be converted to various carbonyl compounds through oxidative cleavage of the C–C bond.

The Journal of Organic Chemistry
Tokyo University of Science (JP)
Support for Pioneering Research Initiated by the Next Generation, Japan Society for the Promotion of Science
Clean water and sanitation
Openalex Percentile: Top 9%
Catalytic C–H Functionalization Methods
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