Conversion of cycloalk-2-enones into 2-methylcycloalkane-1,3-diones - Assessment of various Tamao-Fleming procedures and mechanistic insight into the use of the Me3SiMe2Si unit.
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Yu, G., & Clive, D. L. J. (2016). Conversion of cycloalk-2-enones into 2-methylcycloalkane-1,3-diones - Assessment of various Tamao-Fleming procedures and mechanistic insight into the use of the Me3SiMe2Si unit. Organic and Biomolecular Chemistry, 14(5), 1653–1664. https://doi-org.login.ezproxy.library.ualberta.ca/10.1039/c5ob02402a
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Conjugate addition of Me3SiMe2SiLi to cycloalk-2-en-1-ones, ketalization, Tamao-Fleming oxidation (Bu4NF, then H2O2, KHCO3), TPAP oxidation and acid hydrolysis generates 2-methyl cycloalkane-1,3-diones. Ketalization is needed in order to prevent addition of Me3Si- to the carbonyl. The pentamethyldisilanyl group has advantages over other silicon units that are used in Tamao-Fleming procedures.
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http://purl.org/coar/resource_type/c_6501 http://purl.org/coar/version/c_b1a7d7d4d402bcce http://purl.org/coar/version/c_71e4c1898caa6e32
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en