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Hydrocyanation of unsaturated carbonyl compounds
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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.
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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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