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Phosphinamide-Directed Benzylic Lithiation. Application to the Synthesis of Peptide Building Blocks

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NIAID Data Ecosystem2026-03-06 收录
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https://figshare.com/articles/dataset/Phosphinamide_Directed_Benzylic_Lithiation_Application_to_the_Synthesis_of_Peptide_Building_Blocks/2956072
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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.
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2016-06-03
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