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  • Title: Mitsunobu approach to the synthesis of optically active alpha,alpha-disubstituted amino acids.
    Author: Green JE, Bender DM, Jackson S, O'Donnell MJ, McCarthy JR.
    Journal: Org Lett; 2009 Feb 19; 11(4):807-10. PubMed ID: 19159255.
    Abstract:
    Chiral tertiary alpha-hydroxy esters of known stereochemical configuration were transformed to alpha-azido esters by Mitsunobu reaction with HN3. Optimization of this reaction was shown to proceed at room temperature with high chemical yield using 1,1-(azodicarbonyl)dipiperidine (ADDP) and trimethylphosphine (PMe3). Complete inversion of configuration was observed at the alpha-carbon. Several alpha,alpha-disubstituted amino acids were synthesized in high overall chemical yield and optical purity.
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