Approach to(R)- and (S)-ketone cyanohydrins using almond and apple meal as the source of (R)-oxynitrilase

doi:10.1016/S0957-4166(97)00110-9

Tetrahedron: Asymmetry

Volume 8, Issue 10, 22 May 1997, Pages 1551-1557

https://doi.org/10.1016/S0957-4166(97)00110-9 Get rights and content

Abstract

The synthesis of aliphatic and aromatic (R)-ketone cyanohydrins through the addition of hydrogen cyanide to the corresponding ketones and the synthesis of the (S)-enantiomers through the kinetic resolution of racemic ketone cyanohydrins has been studied in the presence of almond or apple meal. Substrate tolerance of the (R)-oxynitrilases towards ketones (R¹R²C=O) is highly restricted compared to that of structurally similar aldehydes, reactivity following the order of H > Me⪢Et for R². In the case of aromatic methyl ketones reactivity difference (C₆H₅⪢p-MeC₆H₄ for R¹) is notable.

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