Isomerization of 3-unsubstituted 4,5-dihydroisoxazoles over alumina. A new synthesis of β-hydroxy nitriles
作者:S. S. Mochalov、A. N. Fedotov、E. V. Trofimova、R. A. Gazzaeva、N. S. Zefirov
DOI:10.1134/s1070428016030179
日期:2016.3
3-Unsubstituted 4,5-dihydroisoxazoles obtained by nitrosation of arylcyclopropanes are capable of undergoing efficient isomerization into 3-aryl-3-hydroxypropanenitriles during chromatography on alumina.
A facile approach for the synthesis of enantiopure γ-amino nitriles by copper-catalyzed aminocyanation of arylcyclopropanes is disclosed, which undergoes the highly enantioselective ring-opening reaction of cyclopropanes. The strategy utilizes N-fluorobenzenesulfonimide as nucleophilic nitrogen source as well as oxidant and trimethylsilyl cyanide as the other nucleophile, and it probably operates via