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Some hydrogen, carbon, silicon, sulfur, nitrogen and oxygen nucleophiles react diastereoselectively with γ-oxygenated chiral vinyl phosphine oxides to give β-substituted phosphine oxides. Lithium N-benzyl-α-methylbenzylamide adds to prochiral vinyl phosphine oxides in the presence of trimethylsilyl chloride to provide, after protodesilylation, β-amino phosphine oxides as single diastereoisomers.
B. Bartels, J. Clayden, C. Gonzalez Martín, A. Nelson, M. G. Russell and S. Warren, J. Chem. Soc., Perkin Trans. 1, 1999, 1807 DOI: 10.1039/A902414J
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