title: Phosphinamide-directed benzylic lithiation. Application to the synthesis of peptide building blocks.
abstract: N-benzyldiphenylphosphinamides are deprotonated at the NCalpha 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 alpha-, beta-, and gamma-amino acids.
authors.affiliation: Area de Química Orgánica, Universidad de Almería, Carretera de Sacramento s/n, 04120 Almería, Spain.
authors.forename: Pascual Oña
authors.initials: PO
authors.lastname: Burgos
authors.forename: Ignacio
authors.initials: I
authors.lastname: Fernández
authors.forename: María José
authors.initials: MJ
authors.lastname: Iglesias
authors.forename: Santiago
authors.initials: S
authors.lastname: García-Granda
authors.forename: Fernando López
authors.initials: FL
authors.lastname: Ortiz
mesh_terms: D000588:Amines / Q000138:chemical synthesis; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D010647:Phenyl Ethers / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000588:Amines; D000596:Amino Acids; D000605:Amino Alcohols; D001555:Benzene Derivatives; D009943:Organophosphorus Compounds; D010455:Peptides; D010647:Phenyl Ethers; D008094:Lithium