BF3·OEt2-Catalyzed Synthesis of anti-β-(N-Arylamino)-α-hydroxynitriles by Regio- and Diastereospecific Ring Opening of 3-Aryloxirane-2-carbonitriles with Anilines

Abstract A safe and convenient synthetic method to anti -β-( N -arylamino)-α-hydroxynitriles from 3-aryloxirane-2-carbonitriles and anilines was developed under the catalysis of BF 3 ·OEt 2 in ethanol. In this method, BF 3 ·OEt 2 first reacts with ethanol to produce the true catalyst of super­ acid H[B(OEt)F 3 ], followed by an acid-catalyzed regio- and diastereospecific ring opening of oxirane-2-carbonitriles with anilines, generating anti -β-( N -arylamino)-α-hydroxynitriles. The method features the advantages of non-metal catalysis, short reaction times, and easy operation, and uses an environmentally friendly solvent.