Racemic [1SR,2RS,(RS)]-N-cyano(phenyl)methyl-1-aminoindan-2-ol: Crystal structure and reactivity towards thermal epimerization in the solid state

Rumiko Sakurai, Osamu Itoh, Akira Uchida, Tetsutaro Hattori, Sotaro Miyano, Masanori Yamaura

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

A diastereomeric mixture of racemic α-amino nitriles [1SR,2RS,(SR)]- (1) and [1SR,2RS,(RS)]-N-cyano(phenyl)methyl-1-aminoindan-2-ol (2) was thermally epimerized in the solid state to give diastereopure [1SR,2RS,(SR)]-1. The reaction was about 26 times slower than the same reaction of a mixture of their enantiopure counterparts, showing that different mechanisms operated between the two transformations. X-ray crystallographic analysis revealed that in the former transformation, racemic-compound crystals of 2 were converted into conglomerate crystals of 1, while in the latter, enantiomeric crystals of 2 were converted into enantiomeric crystals of 1. The difference in the reactivity toward the epimerization between the racemic and the enantiopure mixture could be rationalized by the difference in the stability of compound 2 in the two crystal forms. Graphical Abstract.

Original languageEnglish
Pages (from-to)10553-10557
Number of pages5
JournalTetrahedron
Volume60
Issue number46 SPEC. ISS.
DOIs
Publication statusPublished - 2004 Nov 8

Keywords

  • Epimerization
  • Solid-state reaction
  • The Strecker reaction
  • cis-1-Aminoindan-2-ol

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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