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23.14.1.2.4 Method 4: Ketones and Vinyl Ethers by Addition of Carbon Nucleophiles to ­Monoalkylketenes

DOI: 10.1055/sos-SD-023-00535

Tidwell, T. T.Science of Synthesis, (200623600.

Monoalkylketenes react readily with Grignard reagents and organolithium compounds to give enolate intermediates.[‌116‌] tert-Butylketene prepared by dehalogenation adds tert-butyllithium to form the enolate 174 that is captured by reaction with chlorotrimethylsilane to give the Z-silyl enol ether 175 through exclusive attack at the position opposite the tert-butyl substituent (Scheme 55).[‌116‌]

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