- 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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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.
- Yu, Guojun,Clive, Derrick L. J.
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p. 1653 - 1664
(2016/02/10)
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- Reactions of 1,2-bis(trimethylsilyloxy)cycloalkenes with the diethyl acetals of aldehydes
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Lewis acid-mediated reactions of 1,2-bis(trimethylsilyloxy)-cyclobutene with acetals derived from a variety of aldehydes, followed by treatment with Amberlyst 15 resin in TFA, yielded 1,3-cyclopentanedione products, but reactions with 3,3-dimethyl-1,2-bis(trimethylsilyloxy)cyclobutene led to 1,2-cyclopentanediones. Reactions of 1,2-bis(trimethylsilyloxy)-cyclopentene gave intermediates that did not undergo skeletal rearrangement with Amberlyst 15 resin in TFA.
- Gao, Fuye,Burnell, D. Jean
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p. 356 - 359
(2007/10/03)
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