One-pot synthesis of α-aminonitriles from alkyl and aryl cyanides

a Strecker reaction via aldimine alanes

Szabolcs Sipos, I. Jablonkai

Research output: Contribution to journalArticle

25 Citations (Scopus)

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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Imines
Cyanides
Phenethylamines
Nitriles
acetone cyanohydrin
triethylamine
diisobutylaluminum

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

One-pot synthesis of α-aminonitriles from alkyl and aryl cyanides : a Strecker reaction via aldimine alanes. / Sipos, Szabolcs; Jablonkai, I.

In: Tetrahedron Letters, Vol. 50, No. 16, 22.04.2009, p. 1844-1846.

Research output: Contribution to journalArticle

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