The Journal of Organic Chemistry

The cyclic dipeptide cyclo [(S)-phenylalanyl-(S)-histidyl] as a catalyst for asymmetric addition of hydrogen cyanide to aldehydes

K Tanaka, A Mori, S Inoue

Index: Tanaka, Kenzo; Mori, Atsunori; Inoue, Shohei Journal of Organic Chemistry, 1990 , vol. 55, # 1 p. 181 - 185

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Citation Number: 216

Abstract

cyclo [(S)-Phenylalanyl-(S)-histidyl](cyclo [(S)-Phe-@)-His], 1) catalyzes the addition of hydrogen cyanide to benzaldehyde in toluene at-20 OC to afford (R)-mandelonitrile with enantiomeric excess of 97% in high yield. cyclo [(R)-Phenylalanyl-(R)-histidyllgives (SI- mandelonitrile. cyclo [(SI-Phe-(&His](1) exhibits a broad substrate specificity, and a variety of aldehydes (3a-r) such as m-methoxybenzaldehyde (3c), 6-methoxy-2-naphthaldehyde (3k ...