Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to Phosphine Ligands for Asymmetric Catalysis

Lu, Zhiwu1,2; Zhang, Haoyang1,2; Yang, Zhiping1,2; Ding, Ning1,2; Meng, Ling1,2,3; Wang, Jun1,2

2019-02

10.1021/acscatal.8b04787

ACS Catalysis   影响因子和分区

2155-5435

Asymmetric hydrophosphination is the most atomically economical and straightforward approach to the construction of chiral organophosphorus compounds. Good stereoselectivities have been achieved in asymmetric hydrophosphination of an electron-deficient C=C double bond, but substrates involving nonpolar C=C bonds remain difficult and are rarely tackled. Herein, we report asymmetric hydrophosphination of a non-electronically activated double bond with a remarkably high degree of stereocontrol. This strategy offered an expedient and broadly applicable platform to prepare tertiary phosphines in high yields (up to 99% yield) and enantioselectivities (up to 99% ee). Particularly noteworthy is that these tertiary phosphine products were then successfully employed as phosphine ligands in enantioselective metal-catalyzed transformations with a high level of asymmetric induction.

asymmetric catalysis hydrophosphination chiral phosphine alkene ligand design

SCI ; EI

英语

第一 ; 通讯

Shenzhen Nobel Prize Scientists Laboratory Project[C17213101]

Chemistry

Chemistry, Physical

WOS:000458707000069

AMER CHEMICAL SOC

20190506443180

Catalysis ; Enantioselectivity ; Olefins ; Phosphorus compounds

Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
3.Hong Kong Univ Sci & Technol, Dept Chem, Hong Kong, Peoples R China

Lu, Zhiwu,Zhang, Haoyang,Yang, Zhiping,et al. Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to Phosphine Ligands for Asymmetric Catalysis[J]. ACS Catalysis,2019,9(2):1457-1463.

Lu, Zhiwu,Zhang, Haoyang,Yang, Zhiping,Ding, Ning,Meng, Ling,&Wang, Jun.(2019).Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to Phosphine Ligands for Asymmetric Catalysis.ACS Catalysis,9(2),1457-1463.

Lu, Zhiwu,et al."Asymmetric Hydrophosphination of Heterobicyclic Alkenes: Facile Access to Phosphine Ligands for Asymmetric Catalysis".ACS Catalysis 9.2(2019):1457-1463.