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Repositorio de la Universidad de Oviedo. > Producción Bibliográfica de UniOvi: RECOPILA > Artículos >

Please use this identifier to cite or link to this item: http://hdl.handle.net/10651/10820

Title: Phosphinamide-directed benzylic lithiation. Application to the synthesis of peptide building blocks
Author(s): Oña Burgos, Pascual
Fernández de las Nieves, Ignacio
Iglesias Valdés-Solís, María José
García-Granda, Santiago
López Ortiz, Fernando
Issue date: 2008
Publisher version: http://dx.doi.org/10.1021/ol7028096
Citation: Organic Letters, 10 (4), p. 537-540 (2008); doi:10.1021/ol7028096
Format extent: p. 537-540
Abstract: N-Benzyldiphenylphosphinamides are deprotonated at the NCα position diastereospecifically upon treatment with t-BuLi in diethyl ether at low temperature. The reaction of the anions with alkyl, acyl, and tin halides, aliphatic and aromatic aldehydes, and Michael acceptors allowed installation of a variety of functional groups into the benzylic arm in excellent yields. Cleavage of the P−N linkage affords 1,2-amino alcohols and α-, β-, and γ-amino acids.
URI: http://hdl.handle.net/10651/10820
ISSN: 1523-7060
Local identifier: 1099
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