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Diastereoselective alkylation of chiral glycinate derivatives containing the ?-phenylethyl group.



Lopez Ruiz, Heraclio

2011

Rodríguez-Garnica Cristina, López-Ruiz Heraclio,* Rojas-Lima Susana, Álvarez-Hernández Alejandro, Tapia-Benavides Rafael, García-López María Concepción. Diastereoselective alkylation of chiral glycinate derivatives containing the ?-phenylethyl group. Journal of the Mexican Chemical Society, 55(3), 148-153. (2011)


Abstract


Novel chiral glycinate derivatives (S)-6 and (S)-7 containing the a-phenylethyl group, were prepared and studied as potential precursors of enantiopure a-substituted-a-amino acids. In particular, the alkylation of enolate (S)-7-Li showed substantial (78:22 dr)stereoinduction by the N-(1-phenylethyl)benzamide chiral auxiliary.Addition of DMPU showed no appreciable effect upon the diastereoselectivity.



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