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Palladium-Catalyzed Enantio- and Regioselective Ring-Opening Hydrophosphinylation of Methylenecyclopropanes |
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| Authors: | Jian Zhou Dr Ling Meng Dr Shujuan Lin Baohua Cai Prof Jun |
| Institution: | 1. Department of Chemistry, Hong Kong Baptist University Kowloon, Hong Kong, China
Department of Chemistry, Southern University of Science and Technology Shenzhen, Guangdong, 518055 China These authors contributed equally to this work.;2. Department of Chemistry, Hong Kong Baptist University Kowloon, Hong Kong, China These authors contributed equally to this work.;3. State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences Fuzhou, Fujian, 350002 China;4. Department of Chemistry, Southern University of Science and Technology Shenzhen, Guangdong, 518055 China;5. Department of Chemistry, Hong Kong Baptist University Kowloon, Hong Kong, China |
| Abstract: | Transition metal-catalyzed hydrofunctionalization of methylenecyclopropanes (MCPs) has presented a considerable challenge due to the difficult manipulation of regioselectivity and complicated reaction patterns. Herein, we report a straightforward Pd-catalyzed ring-opening hydrophosphinylation reaction of MCPs via highly selective C−C bond cleavage. This method allows for rapid and efficient access to a wide range of chiral allylic phosphine oxides in good yields and high enantioselectivities. Additionally, density functional theory (DFT) calculations were performed to elucidate the reaction mechanism and the origin of enantioselectivity. |
| Keywords: | C−C Bond Cleavage C−P Bond Formation DFT Calculations Hydrophosphinylation Phosphine |