Journal of Organic Chemistry p. 181 - 185 (1990)
Update date:2022-08-05
Topics:
Tanaka, Kenzo
Mori, Atsunori
Inoue, Shohei
cyclo<(S)-Phenylalanyl-(S)-histidyl> (cyclo<(S)-Phe-(S)-His>, 1) catalyzes the addition of hydrogen cyanide to benzaldehyde in toluene at -20 deg C to afford (R)-mandelonitrile with enantiomeric excess of 97 percent in high yield. cyclo<(R)-Phenylalanyl-(R)-histidyl> gives (S)-mandelonitrile. cyclo<(S)-Phe-(S)-His> (1) exhibits a broad substrate specificity, and a variety of aldehydes (3a-r) such as m-methoxybenzaldehyde (3c), 6-methoxy-2-naphthaldehyde (3k), and isobutyraldehyde (3o) similarly afforded the corresponding cyanohydrins with high enantiopurities (97 percent ee for 3c, 93 percent ee for 3k, 71 percent ee for 3o). (R)-Mandelonitrile thus obtained was successfully converted to various chiral synthons such as mandelic acid (7), methyl mandelate (8), and 2-amino-1-phenylethanol (9) without any racemization.
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