Journal of the American Chemical Society

Conjugate addition of B-alkenyl-9-borabicyclo [3.3. 1] nonanes to methyl vinyl ketone. A convenient synthesis of. gamma.,. delta.-unsaturated ketones

P Jacob III, H Brown

文献索引：Jacob,P.; Brown,H.C. Journal of the American Chemical Society, 1976 , vol. 98, p. 7832 - 7833

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被引用次数: 39

摘要

B-Alkenyl-9-borabicyclo [3.3. 1] nonanes (B-alkenyl-9-BBN)(l), readily prepared by the hydroboration of acetylenes with 9-BBN,'undergo a smooth 1, Caddition to methyl vinyl ketone (MVK) and related ketones in refluxing tetrahydrofuran. Hydrolysis of the initially formed enol borinate intermediate (2) provides the corresponding 4-alkenyl-2-butanones (3)(eq 1).