1010128-92-3Relevant articles and documents
Phosphinamide-directed benzylic lithiation. application to the synthesis of peptide building blocks
Burgos, Pascual Ona,Fernandez, Ignacio,Iglesias, Maria Jose,Garcia-Granda, Santiago,Ortiz, Fernando Lopez
, p. 537 - 540 (2008)
N-Benzyldiphenylphosphinamides are deprotonated at the NCα position diastereospecifically upon treatment with f-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.