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Determining the absolute configuration of secondary alcohols by means of a chiral auxiliary and NOESY
Authors:Blanca E Domínguez  Patricia E García  Jorge Crdenas
Institution:

aCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, 62210 Cuernavaca, Morelos, Mexico

bInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán 04510, D.F., Mexico

Abstract:The absolute configuration of secondary alcohols can be determined by NOE between the diastereotopic protons of the lactam and the protons of the alcohol moieties in some 1-(alkoxymethyl)-methyl-2-pyrrolidone-5-carboxylate derivatives. Two simple methods based on conformational analysis and 1H NMR data have been developed. The main conformer, in all cases, was established by means of MM, semi-empirical, and ab initio calculations.
Keywords:
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