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

A diastereomeric mixture of racemic α-amino nitriles [1 SR, 2RS,( SR)]- ( 1 ) and [1 SR,2 RS,( RS)]- N-cyano(phenyl)methyl-1-aminoindan-2-ol ( 2 ) was thermally epimerized in the solid state to give diastereopure [1 SR,2 RS,( SR)]- 1 . The reaction was about 26 times slower than the same reaction of...

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Bibliographic Details
Published in:Tetrahedron 2004-11, Vol.60 (46), p.10553-10557
Main Authors: Sakurai, Rumiko, Itoh, Osamu, Uchida, Akira, Hattori, Tetsutaro, Miyano, Sotaro, Yamaura, Masanori
Format: Article
Language:English
Subjects:
cis-1-Aminoindan-2-ol
Epimerization
Solid-state reaction
The Strecker reaction
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Summary:A diastereomeric mixture of racemic α-amino nitriles [1 SR, 2RS,( SR)]- ( 1 ) and [1 SR,2 RS,( RS)]- N-cyano(phenyl)methyl-1-aminoindan-2-ol ( 2 ) was thermally epimerized in the solid state to give diastereopure [1 SR,2 RS,( 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
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.08.084