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  • Title: Diastereoselective preparation of (R)- and (S)-2-methoxy-2-phenylpent-3-ynoic acids and their use as reliable chiral derivatizing agents.
    Author: Pérez-Estrada S, Joseph-Nathan P, Jiménez-Vázquez HA, Medina-López ME, Ayala-Mata F, Zepeda LG.
    Journal: J Org Chem; 2012 Feb 17; 77(4):1640-52. PubMed ID: 22217094.
    Abstract:
    Benzoyl-S,O-acetals 1a and 1b were used as chiral auxiliaries to achieve the diastereoselective preparation of both enantiomers of 2-methoxy-2-phenylpent-3-ynoic acids (MPPAs). The latter were condensed with several chiral secondary alcohols and some primary amines to evaluate their potential as chiral derivatizing agents (CDAs). The (1)H NMR spectra of the corresponding esters and amides showed strong consistency with the absolute configuration of the carbinol and amine moieties, whose observed ΔδL(1) and ΔδL(2) values were in the ranges of 0.1-0.4 and 0.02-0.12 ppm, respectively.
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