Reaction of β-halo α, β-unsaturated ketones with cuprate reagents. Efficient syntheses of β, β-dialkyl ketones and β-alkyl α, β-unsaturated ketones. A synthesis of (Z)- …

E Piers, KF Cheng, I Nagakura

Index: Piers, Edward; Cheng, Kin Fai; Nagakura, Isao Canadian Journal of Chemistry, 1982 , vol. 60, p. 1256 - 1263

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Citation Number: 28

Abstract

Treatment of the 3-halo-2-cyclohexen-1-ones 11-15 and 17 with an excess of lithium dimethylcuprate provided good to excellent yields of the corresponding 3, 3- dimethylcyclohexanones 21-24. Similar reactions involving the β-bromo cyclopentenones 19 and 20 stopped at the monoaddition stage, producing the cyclopentenones 40 and 43. Reaction of the β-bromo cyclohexenones 12 and 15 with 1.1 equiv. of lithium ...

~91%

~86%

~83%

~84%

~74%

~86%

~91%

~63%

~84%

~88%

~82%

~93%

~89%

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