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Phosphinamide-directed benzylic lithiation. Application to the synthesis of peptide building blocks

dc.contributor.authorOña Burgos, Pascual
dc.contributor.authorFernández de las Nieves, Ignacio
dc.contributor.authorIglesias Valdés-Solís, María José
dc.contributor.authorGarcía-Granda, Santiago 
dc.contributor.authorLópez Ortiz, Fernando
dc.date.accessioned2013-01-30T10:21:02Z
dc.date.available2013-01-30T10:21:02Z
dc.date.issued2008
dc.identifier.citationOrganic Letters, 10 (4), p. 537-540 (2008); doi:10.1021/ol7028096spa
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/10651/10820
dc.description.abstractN-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.spa
dc.format.extentp. 537-540spa
dc.language.isoeng
dc.relation.ispartofOrganic Lettersspa
dc.rights(c) American Chemical Society
dc.sourceWOKspa
dc.titlePhosphinamide-directed benzylic lithiation. Application to the synthesis of peptide building blocksspa
dc.typeinfo:eu-repo/semantics/article
dc.identifier.local1099spa
dc.identifier.doi10.1021/ol7028096
dc.type.dcmitextspa
dc.relation.publisherversionhttp://dx.doi.org/10.1021/ol7028096spa


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