Convenient, large-scale asymmetric synthesis of enantiomerically pure trans-cinnamylglycine and -α-alanine

Wei Qiu, Vadim A. Soloshonok, Chaozhong Cai, Xuejun Tang, Victor J. Hruby

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Abstract

Asymmetric syntheses of (S)-trans-cinnamylglycine and (S)-α-trans- cinnamyl-α-alanine via reactions of cinnamyl halides (Cl, Br) with Ni(II)- complexes of the chiral Schiff base of glycine or alanine with (S)-o-[N-(N- benzylprolyl)amino]benzophenone were developed. Inexpensive and readily available reagents and solvents were used, including an easily recyclable chiral auxiliary. The simplicity of the experimental procedures and the high stereochemical outcome make this method synthetically attractive for preparing the target amino acids on multi-gram scales. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)2577-2582
Number of pages6
JournalTetrahedron
Volume56
Issue number17
DOIs
StatePublished - Apr 21 2000

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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