Palladium-Catalyzed Enantio- and Regioselective Ring-Opening Hydrophosphinylation of Methylenecyclopropanes

Zhou, Jian1,2; Meng, Ling1; Lin, Shujuan3; Cai, Baohua2; Wang, Jun (Joelle)1

2023-05-01

10.1002/anie.202303727

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   影响因子和分区

1433-7851

1521-3773

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.

C-C Bond Cleavage C-P Bond Formation DFT Calculations Hydrophosphinylation Phosphine

SCI ; EI ; IC ; CCR

英语

NI论文

其他

Research Grants Council of Hong Kong[GRF 12303422] ; National Natural Science Foundation of China[NSFC 22271241]

Chemistry

Chemistry, Multidisciplinary

WOS:000988179300001

WILEY-V C H VERLAG GMBH

20232014111552

Catalysis ; Chemical bonds ; Density functional theory ; Enantioselectivity ; Palladium ; Phosphorus compounds ; Propane

Precious Metals:547.1 ; Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Probability Theory:922.1 ; Atomic and Molecular Physics:931.3 ; Quantum Theory; Quantum Mechanics:931.4

CHEMISTRY

Web of Science

1.Hong Kong Baptist Univ, Dept Chem, Kowloon, Hong Kong, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
3.Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Fujian, Peoples R China

Zhou, Jian,Meng, Ling,Lin, Shujuan,et al. Palladium-Catalyzed Enantio- and Regioselective Ring-Opening Hydrophosphinylation of Methylenecyclopropanes[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2023,62(26).

Zhou, Jian,Meng, Ling,Lin, Shujuan,Cai, Baohua,&Wang, Jun .(2023).Palladium-Catalyzed Enantio- and Regioselective Ring-Opening Hydrophosphinylation of Methylenecyclopropanes.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,62(26).

Zhou, Jian,et al."Palladium-Catalyzed Enantio- and Regioselective Ring-Opening Hydrophosphinylation of Methylenecyclopropanes".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 62.26(2023).