The formation of bicyclo[n.2.0]alkan-1-ols from the reaction of the lithium enolates of simple ketones and phenyl vinyl sulfoxide
Author(s)
Loughlin, WA
McCleary, MA
Griffith University Author(s)
Year published
2003
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Show full item recordAbstract
The enolates generated from cyclopentanone, cycloheptanone or cyclooctanone and LDA at -78 àin THF react with (ᩭphenyl vinyl sulfoxide under controlled conditions of temperature, reaction time, and concentration. Upon oxidation with MCPBA of the product mixtures, the novel sulfonylbicyclo[3.2.0]heptan-1-ols 10-12, sulfonylbicyclo[5.2.0]nonan-1-ols 16-18, and sulfonylbicyclo[6.2.0]decan-1-ols 21 and 22 in conjunction with alkylated ketones 8, 9, 15, 19 and 20 were obtained from the respective ketones. The enolate generated from cyclobutanone and LDA at -78 àin THF reacts with (ᩭphenyl vinyl sulfoxide and upon oxidation with ...
View more >The enolates generated from cyclopentanone, cycloheptanone or cyclooctanone and LDA at -78 àin THF react with (ᩭphenyl vinyl sulfoxide under controlled conditions of temperature, reaction time, and concentration. Upon oxidation with MCPBA of the product mixtures, the novel sulfonylbicyclo[3.2.0]heptan-1-ols 10-12, sulfonylbicyclo[5.2.0]nonan-1-ols 16-18, and sulfonylbicyclo[6.2.0]decan-1-ols 21 and 22 in conjunction with alkylated ketones 8, 9, 15, 19 and 20 were obtained from the respective ketones. The enolate generated from cyclobutanone and LDA at -78 àin THF reacts with (ᩭphenyl vinyl sulfoxide and upon oxidation with MCPBA, the cyclohexanone 4 and monoalkylated cyclobutanone 5 were obtained. The ratio of bicyclo[n.2.0]alkan-1-ol to alkylated products varied with the ketone enolate, conversion of phenyl vinyl sulfoxide, time, temperature and concentration of reaction and the stability and steric strain of the final bicyclo[n.2.0]alkan-1-ol product.
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View more >The enolates generated from cyclopentanone, cycloheptanone or cyclooctanone and LDA at -78 àin THF react with (ᩭphenyl vinyl sulfoxide under controlled conditions of temperature, reaction time, and concentration. Upon oxidation with MCPBA of the product mixtures, the novel sulfonylbicyclo[3.2.0]heptan-1-ols 10-12, sulfonylbicyclo[5.2.0]nonan-1-ols 16-18, and sulfonylbicyclo[6.2.0]decan-1-ols 21 and 22 in conjunction with alkylated ketones 8, 9, 15, 19 and 20 were obtained from the respective ketones. The enolate generated from cyclobutanone and LDA at -78 àin THF reacts with (ᩭphenyl vinyl sulfoxide and upon oxidation with MCPBA, the cyclohexanone 4 and monoalkylated cyclobutanone 5 were obtained. The ratio of bicyclo[n.2.0]alkan-1-ol to alkylated products varied with the ketone enolate, conversion of phenyl vinyl sulfoxide, time, temperature and concentration of reaction and the stability and steric strain of the final bicyclo[n.2.0]alkan-1-ol product.
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Journal Title
Organic and Biomolecular Chemistry
Volume
1
Publisher URI
Copyright Statement
© 2003 Royal Society Reproduced in accordance with the copyright policy of the publisher. Use hypertext link for access to the journal's website.
Subject
Medicinal and biomolecular chemistry
Organic chemistry