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26844569407
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note
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13C NMR : 22.7; 25.1; 27.2; 35.3; 39.3; 39.8; 56.7; 214.4. MS (m/z) : 152, 111, 95, 81, 67, 55.
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34
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26844459497
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note
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(Chemical Equation Presented)
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37
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26844469283
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note
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The reaction of 2-methylcyclohexanone potassium enolates prepared from ketone 1b (tBuOK (1 eq.), THF, -20°C, 1h) with benzyl bromide (THF, -78°C, 1h) yielded ketone 8b (R = benzyl) with a 38% chromatographed yield. The regioisomeric ketone 9b (R = benzyl) was not detected. A large amount of unreacted ketone Ia was detected by GC in the erode material.
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38
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26844503639
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note
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5 enolates obtained from silyl enol ethers, the alkylation is reported to maintain the structure of the starting silyl enol ether due to the enhanced nucleophilicity of these naked enolates, compared with lithium enolates. The alkylation conditions are also to be noted : the onium enolates are not preformed but obtained in the presence of the alkylating reagent, thus trapped as soon as they are formed, preventing proton transfer and their equilibration before alkylation.
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