1989
DOI: 10.1246/bcsj.62.645
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Acid-Catalyzed Oxidation of Oxiranes with Dimethyl Sulfoxide Giving α-Hydroxy Ketones

Abstract: The reaction of various oxiranes with dimethyl sulfoxide in the presence of Molecular Sieve 4A and acid afforded the corresponding α-hydroxy ketones. The molecular sieve was found to accelerate the reaction.

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Cited by 30 publications
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“…Nevertheless, the highly selective oxidation of ( R , R )- 2c with BDHA gave rise to the formation of ( R )-hydroxycycloheptanone 3c still in excellent ee (99%). In comparison, chemical conversion of epoxides to α-hydroxy ketones with strong acids gave racemic product together with several byproducts. …”
Section: Resultsmentioning
confidence: 99%
“…Nevertheless, the highly selective oxidation of ( R , R )- 2c with BDHA gave rise to the formation of ( R )-hydroxycycloheptanone 3c still in excellent ee (99%). In comparison, chemical conversion of epoxides to α-hydroxy ketones with strong acids gave racemic product together with several byproducts. …”
Section: Resultsmentioning
confidence: 99%