Recent Advances in Transition Metal-Catalyzed Asymmetric Synthesis of P-chiral Organophosphorus Compounds (2020-Present)

被引:0
作者
Liu, Bai-Xue [1 ,2 ]
Feng, Fan [1 ,2 ]
Long, Jiao [1 ,2 ,3 ]
Gu, Shuang-Xi [1 ,2 ,3 ]
机构
[1] Wuhan Inst Technol, Sch Chem Engn & Pharm, Wuhan 430205, Hubei, Peoples R China
[2] Wuhan Inst Technol, Hubei Key Lab Novel Reactor & Green Chem Technol, Wuhan 430205, Hubei, Peoples R China
[3] Minist Educ, Wuhan Inst Technol, Key Lab Green Chem Proc, Wuhan 430205, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
P-Chirality; Phosphination reaction; Hydrophosphination reaction; Asymmetric synthesis; Organophosphorus compounds; Enantioselectivity; Stereochemistry; SECONDARY PHOSPHINE OXIDES; LIGANDS; HYDROGENATION; ARYLATION; PROGRESS; FACILE;
D O I
10.1002/cjoc.70093
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
P-chiral organophosphorus compounds have demonstrated unparalleled application potential in diverse fields, including medicine, agricultural science, material science, and life science. Furthermore, they serve as highly effective chiral ligands in both transition metal-catalyzed and organocatalytic asymmetric transformations. In recent years, significant advances have been made in the catalytic asymmetric synthesis of P-chiral organophosphorus compounds, with asymmetric phosphination and hydrophosphination reactions emerging as the dominant strategies. This review systematically summarizes the methodological developments from 2020 to present for constructing P-chiral organophosphorus compounds. The discussion is organized according to different transition metals, aiming to provide a valuable reference and inspiration for researchers in organic synthesis and organophosphorus chemistry.
引用
收藏
页码:2228 / 2244
页数:17
相关论文
共 80 条
[1]   Optimizing phosphorus fertilizer use to enhance water quality, food security and social equality [J].
Bai, Zhaohai ;
Liu, Ling ;
Kroeze, Carolien ;
Strokal, Maryna ;
Chen, Xinping ;
Yuan, Zengwei ;
Ma, Lin .
RESOURCES CONSERVATION AND RECYCLING, 2024, 203
[2]   Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines [J].
Beaud, Rodolphe ;
Phipps, Robert J. ;
Gaunt, Matthew J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (40) :13183-13186
[3]   Ni-Catalyzed Enantioselective Benzylation of Secondary Phosphine Oxide [J].
Cai, Wen-Qiang ;
Wei, Qi ;
Zhang, Qing-Wei .
ORGANIC LETTERS, 2022, 24 (05) :1258-1262
[4]   Asymmetric catalytic synthesis of P-stereogenic phosphines via a nucleophilic ruthenium phosphido complex [J].
Chan, VS ;
Stewart, IC ;
Bergman, RG ;
Toste, FD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (09) :2786-2787
[5]   Collective synthesis of acetylenic pharmaceuticals via enantioselective Nickel/Lewis acid-catalyzed propargylic alkylation [J].
Chang, Xihao ;
Zhang, Jiayin ;
Peng, Lingzi ;
Guo, Chang .
NATURE COMMUNICATIONS, 2021, 12 (01)
[6]   Our Odyssey with Functionalized Chiral Phosphines: From Optical Resolution to Asymmetric Synthesis to Catalysis [J].
Chew, Renta Jonathan ;
Leung, Pak-Hing .
CHEMICAL RECORD, 2016, 16 (01) :141-158
[7]   Ni-Catalyzed Asymmetric C-P Cross-Coupling Reaction for the Synthesis of Chiral Heterocyclic Phosphine Oxides [J].
Cui, Ranran ;
Wang, Yinqi ;
Yuwen, Liyan ;
Gao, Li ;
Huang, Zhuo ;
Wang, Wei-Han ;
Zhang, Qing-Wei .
ORGANIC LETTERS, 2023, :6139-6142
[8]   Palladium/Xiao-Phos-Catalyzed Kinetic Resolution of sec-Phosphine Oxides by P-Benzylation [J].
Dai, Qiang ;
Liu, Lu ;
Zhang, Junliang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (52) :27247-27252
[9]   Construction of P-Chiral Alkenylphosphine Oxides through Highly Chemo-, Regio-, and Enantioselective Hydrophosphinylation of Alkynes [J].
Dai, Qiang ;
Liu, Lu ;
Qian, Yanyan ;
Li, Wenbo ;
Zhang, Junliang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (46) :20645-20650
[10]   P-Chiral Phosphines Enabled by Palladium/Xiao-Phos-Catalyzed Asymmetric P-C Cross-Coupling of Secondary Phosphine Oxides and Aryl Bromides [J].
Dai, Qiang ;
Li, Wenbo ;
Lo, Zhiming ;
Zhang, Junliang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (51) :20556-20564