title: Epimerization of diastereomeric alpha-amino nitriles to single stereoisomers in the solid state.
abstract: [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.
authors.affiliation: Department of Environmental Studies, Graduate School of Environmental Studies, Tohoku University, Aramaki-Aoba 07, Aoba-ku, Sendai 980-8579, Japan.
authors.forename: Rumiko
authors.initials: R
authors.lastname: Sakurai
authors.forename: Shuji
authors.initials: S
authors.lastname: Suzuki
authors.forename: Junichi
authors.initials: J
authors.lastname: Hashimoto
authors.forename: Manabu
authors.initials: M
authors.lastname: Baba
authors.forename: Osamu
authors.initials: O
authors.lastname: Itoh
authors.forename: Akira
authors.initials: A
authors.lastname: Uchida
authors.forename: Tetsutaro
authors.initials: T
authors.lastname: Hattori
authors.forename: Sotaro
authors.initials: S
authors.lastname: Miyano
authors.forename: Masanori
authors.initials: M
authors.lastname: Yamaura