One-pot synthesis of α-aminonitriles from alkyl and aryl cyanides: a Strecker reaction via aldimine alanes

Szabolcs Sipos, István Jablonkai

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Abstract

A one-pot Strecker reaction using various alkyl, arylalkyl and arylnitriles is developed. Aldimine alanes were generated in situ from nitriles by the addition of diisobutylaluminium hydride, and were converted into the corresponding imines on reaction with (S)-(-)-1-phenylethylamine. Nucleophilic addition to the imines in the presence of catalytic triethylamine, using acetone cyanohydrin as a cyanide source, provided α-aminonitriles.

Original languageEnglish
Pages (from-to)1844-1846
Number of pages3
JournalTetrahedron Letters
Volume50
Issue number16
DOIs
Publication statusPublished - Apr 22 2009

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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