Trityl Cation-Catalyzed Hosomi-Sakurai Reaction of Allylsilane with β,γ-Unsaturated α-Ketoester to Form γ,γ-Disubstituted α-Ketoesters

Zubao Gan; Deyun Cui; Hongyun Zhang; Ying Feng; Liying Huang; Yingying Gui; Lu Gao; Zhenlei Song

doi:10.3390/molecules27154730

Trityl Cation-Catalyzed Hosomi-Sakurai Reaction of Allylsilane with β,γ-Unsaturated α-Ketoester to Form γ,γ-Disubstituted α-Ketoesters

Molecules. 2022 Jul 24;27(15):4730. doi: 10.3390/molecules27154730.

Authors

Zubao Gan¹, Deyun Cui¹, Hongyun Zhang¹, Ying Feng¹, Liying Huang¹, Yingying Gui¹, Lu Gao¹, Zhenlei Song¹

Affiliation

¹ Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.

Abstract

(Ph₃C)[BPh(^F)₄]-catalyzed Hosomi-Sakurai allylation of allylsilanes with β,γ-unsaturated α-ketoesters has been developed to give γ,γ-disubstituted α-ketoesters in high yields with excellent chemoselectivity. Preliminary mechanistic studies suggest that trityl cation dominates the catalysis, while the silyl cation plays a minor role.

Keywords: Hosomi-Sakurai allylation; allylsilane; trityl cation; α-ketoester.

MeSH terms

Alkenes
Catalysis
Cations
Molecular Structure
Silanes
Stereoisomerism*

Substances

Alkenes
Cations
Silanes
allylsilane

Abstract

MeSH terms

Substances

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