Communication
Palladium/Xiao-Phos-Catalyzed Kinetic Resolution of sec-Phosphine Oxides by P-Benzylation
Qiang Dai,
Prof. Lu Liu,
Prof. Junliang Zhang,
Qiang Dai
School of Chemistry and Molecular Engineering and Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200241 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Lu Liu
School of Chemistry and Molecular Engineering and Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200241 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Junliang Zhang
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai, 200438 P. R. China
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 P. R. China
Search for more papers by this authorQiang Dai,
Prof. Lu Liu,
Prof. Junliang Zhang,
Qiang Dai
School of Chemistry and Molecular Engineering and Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200241 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Lu Liu
School of Chemistry and Molecular Engineering and Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai, 200241 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Junliang Zhang
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai, 200438 P. R. China
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007 P. R. China
Search for more papers by this authorDedicated to 70th anniversary of East China Normal University
Graphical Abstract
A kinetic resolution of rac-secondary phosphine oxides via the enantioselective P-benzylation process catalyzed by the palladium/Xiao-Phos was designed. Both, tert- and sec-phosphine oxides were delivered in good yield and excellent enantiopurity (selectivity factor up to 226.1). The synthetic utilities are further demonstrated by the facile preparation of several P-chiral compounds, precursors of bidentate ligands, and transition metal complexes.
Abstract
P-stereogenic tert- and sec-phosphines have wide applications in asymmetric catalysis, materials, and pharmaceutical chemistry, however, their practical synthesis still constitutes a significant challenge. Herein, a successful kinetic resolution of rac-secondary phosphine oxides via the enantioselective P-benzylation process catalyzed by the palladium/Xiao-Phos was designed. Both tert- and sec-phosphine oxides were delivered in good yield and excellent enantiopurity (selectivity factor up to 226.1). The appealing synthetic utilities are further demonstrated by the facile preparation of several valuable P-chiral compounds, precursors of bidentate ligands, as well as transition metal complexes.
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