Base-induced. alpha.-alkenylation of ethyl bromoacetate, phenacyl bromide and chloroacetonitrile via B-trans-1-alkenyl-9-borabicyclo [3.3. 1] nonanes

HC Brown, NG Bhat, JB Campbell Jr

Index: Brown, Herbert C.; Bhat, Narayan G.; Campbell, James B. Journal of Organic Chemistry, 1986 , vol. 51, # 17 p. 3398 - 3400

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Citation Number: 25

Abstract

Summary: B-trans-l-Alkenyl-9-borabicyclo [3.3. l] nonanes, easily and quantitatively prepared by the reaction of 9-BBN with various 1-alkynes in tetrahydrofuran, undergo facile reaction with a-halo carbanions generated from ethyl bromoacetate, phenacyl bromide, and chloroacetonitrile in the presence of potassium 2, 6-di-tert-butylphenoxide, providing the corresponding P, y-unsaturated esters, ketones, and nitriles in good yield.

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