PREPARATION OF SILYL ENOL ETHERS DERIVED FROM ALPHA-PHENYLSELENO ALDEHYDES AND ALPHA-PHENYLSELENO KETONES
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PONTHIEUX, S
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UNIV ROUEN,UFR SCI,IRCOF,SYNTH HETEROORGAN LAB,F-76821 MONT ST AIGNAN,FRANCEUNIV ROUEN,UFR SCI,IRCOF,SYNTH HETEROORGAN LAB,F-76821 MONT ST AIGNAN,FRANCE
PONTHIEUX, S
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OUTURQUIN, F
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UNIV ROUEN,UFR SCI,IRCOF,SYNTH HETEROORGAN LAB,F-76821 MONT ST AIGNAN,FRANCEUNIV ROUEN,UFR SCI,IRCOF,SYNTH HETEROORGAN LAB,F-76821 MONT ST AIGNAN,FRANCE
OUTURQUIN, F
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PAULMIER, C
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UNIV ROUEN,UFR SCI,IRCOF,SYNTH HETEROORGAN LAB,F-76821 MONT ST AIGNAN,FRANCEUNIV ROUEN,UFR SCI,IRCOF,SYNTH HETEROORGAN LAB,F-76821 MONT ST AIGNAN,FRANCE
PAULMIER, C
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[1] UNIV ROUEN,UFR SCI,IRCOF,SYNTH HETEROORGAN LAB,F-76821 MONT ST AIGNAN,FRANCE
The best experimental conditions for the preparation of trimethylsilyl enol ethers 3 from alpha-phenylseleno aldehydes 1, compatible with a limited deselenenylation of the substrate, were studied. Starting from alpha-phenylseleno ketones 2, the enoxysilanes 4, bearing a vinylic PhSe group, are the major products when triethylamine is the base. Trimethylsilyl enol ethers 5 with an allylic PhSe group are also formed beside 4 when LDA or KH are used at lower temperatures.