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Synlett 2000; 2000(11): 1553-1556
DOI: 10.1055/s-2000-7946
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Stereocontrolled Synthesis of Multi-functionalized β-Substituted α-Amino Acids: Nitrone Cycloaddition Approach

Osamu Tamura* , Satoshi Yoshida, Hiroaki Sugita, Naka Mita, Yumiko Uyama, Nobuyoshi Morita, Masaji Ishiguro, Tomomi Kawasaki, Hiroyuki Ishibashi, Masanori Sakamoto
  • *Faculty of Pharmaceutical Sciences, Kanazawa University, Takaramachi, Kanazawa 920-0934, Japan
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Publication Date:
31 December 2000 (online)

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Syn- and anti-β-substituted α-amino acids 1 and 2 were synthesized by employing nitrone-cycloaddition. The stereochemistries required were controlled via a (Z)-nitrone-exo transition state for syn-amino acid 1 and via an (E)-nitrone-exo transition state for anti-amino acid 2, respectively.

amino acid - asymmetric synthesis - chiral auxiliary - cycloaddition - tandem reaction