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Synlett 1991; 1991(4): 263-264
DOI: 10.1055/s-1991-20701
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Essential Factors in Asymmetric Hydrocyanation Catalyzed by Cyclo(-(R)-Phe-(R)-His-)

Hidenori Danda*
  • *Takarazuka Research Center, Sumitomo Chemical Co., Ltd., 2-1, 4-Chome, Takatsukasa, Takarazuka, Hyogo 665, Japan
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Publication Date:
07 March 2002 (online)

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In the asymmetric hydrocyanation of 3-phenoxybenzaldehyde to (S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile catalyzed by the cyclic dipeptide cyclo(-(R)-Phe-(R)-His-) 2, it was essential for high enantioselectivity to make the catalyst 2 completely amorphous, so that the reaction mixture is a clear gel. However, the choice of solvents for the activation of 2 is not essential. It was also found that the reaction mixture has thixotropy which has an important influence on the enantioselectivity, that is, the enantioselectivity is raised as the viscosity of the reaction mixture is lowered.

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