Bulletin of the Chemical Society of Japan p. 2851 - 2860 (1986)
Update date:2022-08-11
Topics:
Tsuge, Otohiko
Kanemasa, Shuji
Suzuki, Toshiro
Matsuda, Koyo
Reaction of 1-diazo-3-trimethylsilylpropanone with olefins in the presence of cupric acetylacetonate (Cu(acac)2) affords cyclopropyl trimethylsilylmethyl ketones.One-flask procedure for the formation of these silylated ketones and subsequent treatment with organometallics or with lithium diisopropylamide (LDA) and then carbonyl compounds gives a variety of vinylcyclopropanes or cyclopropyl vinyl ketones in good yields, respectively.Cycloaddition of 1-diazo-3-trimethylsilylpropanone with acetylenes and similar carbon-carbon bond formation at the side chain of the cycloadducts lead to 3-pyrazolyl vinyl ketones.
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