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

Guojun Yu; Derrick L. J. Clive

doi:10.1039/C5OB02402A

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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†

Guojun Yu^a and Derrick L. J. Clive*^a

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^a Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada
E-mail: derrick.clive@ualberta.ca
Fax: +1 (780) 492 8231
Tel: +1 (780) 492 3251

Abstract

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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Article information

DOI: https://doi.org/10.1039/C5OB02402A
Article type: Paper
Submitted: 22 Nov 2015
Accepted: 15 Dec 2015
First published: 15 Dec 2015

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Org. Biomol. Chem., 2016,14, 1653-1664

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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

G. Yu and D. L. J. Clive, Org. Biomol. Chem., 2016, 14, 1653 DOI: 10.1039/C5OB02402A

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Organic & Biomolecular Chemistry