Equatorial preference in the GaCl3-promoted ethenylation of cyclic ketones

M. Arisawa; C. Miyagawa; M. Yamaguchi

doi:10.1055/s-2002-19298

Equatorial preference in the GaCl₃-promoted ethenylation of cyclic ketones

M. Arisawa, C. Miyagawa, M. Yamaguchi

Research output: Contribution to journal › Review article › peer-review

19 Citations (Scopus)

Abstract

Silyl enol ethers derived from substituted cyclohexanones are ethenylated with trimethylsilylethyne in the presence of GaCl₃. Carbon-carbon bond formation was completed in less than 5 min at room temperature and protodegallation of the organogallium intermediate formed with 6 M sulfuric acid gave β-enones. The reactions exhibit a bias for the equatorial C-C bond formation, which contrasts the axial stereochemistry of enolate alkylation. The origin of this stereoselectivity is discussed.

Original language	English
Pages (from-to)	138-145
Number of pages	8
Journal	Synthesis
Issue number	1
DOIs	https://doi.org/10.1055/s-2002-19298
Publication status	Published - 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

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abstract = "Silyl enol ethers derived from substituted cyclohexanones are ethenylated with trimethylsilylethyne in the presence of GaCl3. Carbon-carbon bond formation was completed in less than 5 min at room temperature and protodegallation of the organogallium intermediate formed with 6 M sulfuric acid gave β-enones. The reactions exhibit a bias for the equatorial C-C bond formation, which contrasts the axial stereochemistry of enolate alkylation. The origin of this stereoselectivity is discussed.",

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AU - Miyagawa, C.

AU - Yamaguchi, M.

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N2 - Silyl enol ethers derived from substituted cyclohexanones are ethenylated with trimethylsilylethyne in the presence of GaCl3. Carbon-carbon bond formation was completed in less than 5 min at room temperature and protodegallation of the organogallium intermediate formed with 6 M sulfuric acid gave β-enones. The reactions exhibit a bias for the equatorial C-C bond formation, which contrasts the axial stereochemistry of enolate alkylation. The origin of this stereoselectivity is discussed.

AB - Silyl enol ethers derived from substituted cyclohexanones are ethenylated with trimethylsilylethyne in the presence of GaCl3. Carbon-carbon bond formation was completed in less than 5 min at room temperature and protodegallation of the organogallium intermediate formed with 6 M sulfuric acid gave β-enones. The reactions exhibit a bias for the equatorial C-C bond formation, which contrasts the axial stereochemistry of enolate alkylation. The origin of this stereoselectivity is discussed.

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DO - 10.1055/s-2002-19298

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