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

Article abstract of DOI:10.1055/s-0039-1690243

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.