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Phosphinamide-Directed Benzylic Lithiation. Application to the Synthesis of Peptide Building Blocks

Pascual Oña Burgos, Ignacio Fernández, María José Iglesias, Santiago García-Granda and Fernando López Ortiz*

*Área de Química Orgánica, Universidad de Almería, Carretera de Sacramento s/n, 04120 Almería, Spain, Email: flortizual.es

P. O. Burgos, I. Fernández, M. J. Iglesias, S. García-Granda, F. L. Ortiz, Org. Lett., 2008, 10, 537-540.

DOI: 10.1021/ol7028096 (free Supporting Information)


Abstract

N-Benzyldiphenylphosphinamides are deprotonated at the NCα position diastereospecifically upon treatment with t-BuLi in diethyl ether at low temperature. Reaction of the anions with various electrophiles and subsequent cleavage of the P-N linkage affords 1,2-amino alcohols and α-, β-, and γ-amino acids.


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Key Words

Benzylamines, 1,2-Amino Alcohols, β-Amino Acids


ID: J54-Y2008-0420