Chiral Organosilicon Compounds, Part 3. Peracid Oxidation of Chiral Silyl Enol Ethers

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• The α-siloxyketones do not appear to be hydrolysed by the 5% aq. Na2CO3 used in the work-up
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• The α-siloxyketones (2), while isolable, nevertheless tended to decompose [within hours in the case of the cyclohexanone derivative (2a)]
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• The issue of asymmetric induction does not arise in the synthesis of the α-siloxypinacolone system (2e) since no new chiral centre is generated in this case.
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• At 500 MHz, the inherent non-equivalence of the silyl methyl groups in each diastereomer is presumably reflected in further splitting of some of the SiMe signals.
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• Digitisation of photo-enlarged 60 MHz 1H NMR signals was effected on a Summagraphics ID Data Tablet/Digitiser and relative peak areas were calculated using a Modula-2 programme.
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• Based on curve digitisation and resolution15,16 of 60 MHz and/or spectrometer integration of high-field (300 or 500 MHz) NMR signals.
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