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Hydrocyanation of unsaturated carbonyl compounds : ウィキペディア英語版 | Hydrocyanation of unsaturated carbonyl compounds Hydrocyanation of unsaturated carbonyl compounds is a special case of the Michael reaction which can lead to β-cyanoketones, β-cyano-cyanohydrins, or vinyl cyanohydrins. Fine-tuning reaction conditions allows access to any of these products.〔Nagata, W.; Yoshioka, M. ''Org. React.'' 1977, ''25'', 255. 〕 ==Introduction== Hydrocyanation refers to the addition of the elements of hydrogen and cyanide across a multiple bond. When the multiple bond is polarized by an electron-withdrawing group, selective addition results. However, when the electron-withdrawing group is a carbonyl, the possibility of 1,2 (direct) addition to the carbonyl group exists. Methodological advances now permit access to both direct and conjugate addition products. ''(1)''357px Diastereoselectivity can be achieved in prochiral, conformationally restricted substrates. Catalytic, enantioselective methods, however, are rare.〔Sammis, G.M.; Danjo, H.; Jacobsen, E.N. ''J. Am. Chem. Soc.'' 2004, ''126'', 9928.〕
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