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  • Title: Phosphinamide-directed benzylic lithiation. Application to the synthesis of peptide building blocks.
    Author: Burgos PO, Fernández I, Iglesias MJ, García-Granda S, Ortiz FL.
    Journal: Org Lett; 2008 Feb 21; 10(4):537-40. PubMed ID: 18205370.
    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.
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