High stereocontrol in the allylation of chiral non-racemic α-alkoxy and α-amino nitrones |
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| Authors: | Pedro Merino Ignacio Delso Vanni Mannucci Tomas Tejero |
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| Institution: | Laboratorio de Sintesis Asimetrica, Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragon, Facultad de Ciencias, Universidad de Zaragoza, Consejo Superior de Investigaciones Cientificas, E-50009 Zaragoza, Aragon, Spain |
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| Abstract: | The stereocontrolled addition of allylic metals to chiral non-racemic nitrones promoted by the addition of Lewis acids is described. Whereas for α-alkoxy nitrones the stereocontrol depends on the Lewis acid used as an activator, for α-amino nitrones the diastereofacial course of the reaction depends on the protection of the α-amino group. The successful implementation of the methodology is represented by the enantiodivergent synthesis of d- and l-allylglycine. |
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