Synthesis of Enantioenriched 2- and 2,6-Substituted Piperidin-3-ols from α-Dibenzylamino Aldehydes

Authors

  • José M. Andrés,

    1. Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Doctor Mergelina s/n, 47011 Valladolid, Spain, Fax: +34-983-423013
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  • Rafael Pedrosa,

    1. Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Doctor Mergelina s/n, 47011 Valladolid, Spain, Fax: +34-983-423013
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  • Alfonso Pérez-Encabo

    1. Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Doctor Mergelina s/n, 47011 Valladolid, Spain, Fax: +34-983-423013
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  • Dedicated to Professor Joan Bosch on occasion of his 60th birthday

Abstract

Homochiral α-dibenzylamino aldehydes react with 4-butenylmagnesium bromide in diethyl ether at 0 °C to yield anti-β-amino alcohols in excellent yield and dr. These anti diastereoisomers were transformed into enantioenriched 2- and 2,6-substituted 3-piperidinols in good yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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