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

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• 作者：Sakurai ; Rumiko ; Itoh ; Osamu ; Uchida ; Akira ; Hattori ; Tetsutaro ; Miyano ; Sotaro ; Yamaura ; Masanori
• 关键词：The Strecker reaction ; Epimerization ; Solid-state reaction ; cis-1-Aminoindan-2-ol
• 刊名：Tetrahedron
• 出版年：2004
• 出版时间：November 8, 2004
• 年：2004
• 卷：60
• 期：46
• 页码：10553-10557
• 全文大小：211 K

文摘

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.