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Synthesis of both enantiomers of β,β-diphenyl-α-alanine (Dip) from glycine using (S)- or (R)-2-[(N-benzylprolyl)amino]benzophenone as a reusable chiral auxiliary

✍ Scribed by Vitali I Tararov; Tatyana F Savel'eva; Nickolai Yu Kuznetsov; Nikolai S Ikonnikov; Svetlana A Orlova; Yuri N Belokon; Michael North

Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 323 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(96)00498-3

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✦ Synopsis

Preparative syntheses of enantiopure (S)-and (R)-Dip by et-C-alkylation with Ph2CHX (X=C1 or Br) of the glycine moiety in a Ni(II) Schiff's base complex 1 derived from glycine and (S)-or (R)-[(N-benzylprolyl)amino]benzophenone (BPB) is described. The diastereoselectivity of the alkylation with PhCH2Br in DMF in the presence of NaOH is both kinetically and thermodynamically controlled. (~

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✍ Oleg V. Larionov; Tatyana F. Savel'eva; Konstantin A. Kochetkov; Nikolai S. Ikon 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 English ⚖ 215 KB