Copper-catalyzed asymmetric carbonylative hydroallylation of vinylarenes

We describe a novel and efficient copper-catalyzed carbonylative hydroallylation of vinylarenes, providing a direct route to chiral α,β-unsaturated ketones, which are important compounds in organic synthesis and bioactive molecules. The method employs readily accessible vinylarenes and allylic phosphates, utilizing carbon monoxide as the carbonyl source under mild reaction conditions. The reaction demonstrates a broad substrate scope, including diverse vinylarenes with various functional groups, as well as vinylarenes derived from natural products. Additionally, all four stereoisomers of a chiral allylic alcohol were prepared by employing this strategy, showcasing its versatility in stereodivergent synthesis.

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Publication Details

Journal
Chemical Science
Published
2025-01-01
DOI
https://doi.org/10.1039/d5sc02421h
Citations
12
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
11.23

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article

Copper-catalyzed asymmetric carbonylative hydroallylation of vinylarenes

Yuan Yang, Xiao‐Feng Wu, Sufang Shao, Alban Schmoll
12 citations
Chemical Science
Catalytic C–H Functionalization Methods
11.23
article

Copper-catalyzed asymmetric carbonylative hydroallylation of vinylarenes

Yuan Yang, Xiao‐Feng Wu, Sufang Shao, Alban Schmoll
article en
12 citations

Abstract

We describe a novel and efficient copper-catalyzed carbonylative hydroallylation of vinylarenes, providing a direct route to chiral α,β-unsaturated ketones, which are important compounds in organic synthesis and bioactive molecules. The method employs readily accessible vinylarenes and allylic phosphates, utilizing carbon monoxide as the carbonyl source under mild reaction conditions. The reaction demonstrates a broad substrate scope, including diverse vinylarenes with various functional groups, as well as vinylarenes derived from natural products. Additionally, all four stereoisomers of a chiral allylic alcohol were prepared by employing this strategy, showcasing its versatility in stereodivergent synthesis.

Chemical ScienceVol. 16(24)
Dalian Institute of Chemical Physics (CN), Chinese Academy of Sciences (CN), Nankai University (CN), Leibniz Institute for Catalysis (DE), Dalian National Laboratory for Clean Energy (CN)
National Natural Science Foundation of China, Chinese Academy of Sciences, National Key Research and Development Program of China
Openalex Percentile: Top 1%
Catalytic C–H Functionalization Methods
11.23
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