Epimerization of diastereomeric alpha-amino nitriles to single stereoisomers in the solid state.
[reaction: see text] A diastereomeric mixture of the alpha-amino nitrile prepared by the Strecker reaction of benzaldehyde, (1S,2R)-1-aminoindan-2-ol, and cyanotrimethylsilane thermally epimerizes in the solid state to give a single diastereomer with an (S)-configuration at the alpha position to the nitrile moiety. This shows a sharp contrast to the reaction conducted in DMSO at room temperature, which gives a 1:1 mixture of (S)- and (R)-isomers. Several other alpha-amino nitriles also epimerize in the solid-state toward single diastereomers.
Sakurai
Rumiko
R
Department of Environmental Studies, Graduate School of Environmental Studies, Tohoku University, Aramaki-Aoba 07, Aoba-ku, Sendai 980-8579, Japan.
Suzuki
Shuji
S
Hashimoto
Junichi
J
Baba
Manabu
M
Itoh
Osamu
O
Uchida
Akira
A
Hattori
Tetsutaro
T
Miyano
Sotaro
S
Yamaura
Masanori
M