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Retro‐ Corey‐Chaykovsky Epoxidation: Converting Geminal Disubstituted Epoxides to Ketones
Author(s) -
Li Siqi,
Li Pingfan,
Xu Jiaxi
Publication year - 2019
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201900164
Subject(s) - chemistry , geminal , sulfonium , mesitylene , methylene , organic chemistry , medicinal chemistry , catalysis , salt (chemistry)
Corey‐Chaykovsky epoxidation has been widely applied in the conversion of aldehydes and ketones to epoxides with sulfonium and sulfoxonium ylides. The reverse transformation is realized for conversion of geminal disubstituted epoxides to ketones in the presence of DABCO in refluxing mesitylene. The method is a weak basic transformation from epoxides to ketones with loss of a methylene group and can be applied as an alternative strategy of the acid‐catalyzed Meinwald rearrangement or oxidation for conversion of epoxides to carbonyl compounds.