Cobalt-Catalysed Asymmetric Addition and Alkylation of Secondary Phosphine Oxides for the Synthesis of P-Stereogenic Compounds
Zeng-Hua Wu
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorAn-Qi Cheng
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorMeng Yuan
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorYa-Xuan Zhao
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorHuai-Lan Yang
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorLi-Hua Wei
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorHuai-Yu Wang
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorDr. Tao Wang
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zunting Zhang
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Wei-Liang Duan
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
College of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Road, Yangzhou, 225002 China
Search for more papers by this authorZeng-Hua Wu
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorAn-Qi Cheng
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorMeng Yuan
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorYa-Xuan Zhao
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorHuai-Lan Yang
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorLi-Hua Wei
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorHuai-Yu Wang
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorDr. Tao Wang
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zunting Zhang
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Wei-Liang Duan
School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119 China
College of Chemistry and Chemical Engineering, Yangzhou University, 180 Siwangting Road, Yangzhou, 225002 China
Search for more papers by this authorGraphical Abstract
The catalytic asymmetric synthesis of P-chiral phosphorus compounds is an important way to construct P-chiral ligands. Herein, we report a new strategy that adopts the pyridinyl moiety as the coordinating group in the cobalt-catalysed asymmetric nucleophilic addition/alkylation of secondary phosphine oxides (SPOs). A series of tertiary phosphine oxides (TPOs) were generated with up to 99 % yield and 99.5 % ee, and with broad functional-group tolerance.
Abstract
The catalytic asymmetric synthesis of P-chiral phosphorus compounds is an important way to construct P-chiral ligands. Herein, we report a new strategy that adopts the pyridinyl moiety as the coordinating group in the cobalt-catalysed asymmetric nucleophilic addition/alkylation of secondary phosphine oxides. A series of tertiary phosphine oxides were generated with up to 99 % yield and 99.5 % ee, and with broad functional-group tolerance. Mechanistic studies reveal that (R)-secondary phosphine oxides preferentially interact with the cobalt catalysts to produce P-stereogenic compounds.
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