Epimerization of diastereomeric α-amino nitriles to single stereoisomers in the solid state

Rumiko Sakurai, Shuji Suzuki, Junichi Hashimoto, Manabu Baba, Osamu Itoh, Akira Uchida, Tetsutaro Hattori, Sotaro Miyano, Masanori Yamaura

Research output: Contribution to journalArticlepeer-review

34 Citations (Scopus)

Abstract

A diastereomeric mixture of the α-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 α 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 α-amino nitriles also epimerize in the solid-state toward single diastereomers.

Original languageEnglish
Pages (from-to)2241-2244
Number of pages4
JournalOrganic letters
Volume6
Issue number13
DOIs
Publication statusPublished - 2004 Jun 24

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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