Copper-Catalyzed Dynamic Kinetic Resolution of Secondary Phosphine Oxides

被引:20
作者
Liu, Baixue [1 ,2 ]
Liu, Peng [2 ,3 ]
Wang, Xue [1 ,2 ]
Feng, Feng [1 ,2 ]
Wang, Zhen [1 ,2 ]
Yang, Wenqiang [1 ,2 ]
机构
[1] Linyi Univ, Coll Med, Linyi 276000, Shandong, Peoples R China
[2] Linyi Univ, Coll Chem & Chem Engn, Linyi 276000, Shandong, Peoples R China
[3] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth GIBH, Guangzhou 510530, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
P-STEREOGENIC PHOSPHINES; ENANTIOSELECTIVE SYNTHESIS; ARYLATION;
D O I
10.1021/acs.orglett.3c00099
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-catalyzed dynamic kinetic resolution of secondary phosphine oxides has been successfully developed, providing a general method for the gram-scale enantioselective synthesis of P-stereogenic cyclic phosphine oxides with high yields and high enantioselectivities. The products could be easily reduced to the corresponding useful P(III)-stereogenic cyclic phosphines. A mechanism of the dynamic kinetic resolution involving the unusual rapid racemization of SPOs has been proposed.
引用
收藏
页码:2178 / 2183
页数:6
相关论文
共 40 条
  • [1] Platinum-Catalyzed Enantioselective Tandem Alkylation/Arylation Phosphines. Asymmetric Synthesis of Primary P-Stereogenic 1-Phosphaacenaphthenes
    Anderson, Brian J.
    Guino-O, Marites A.
    Glueck, David S.
    Golen, James A.
    DiPasquale, Antonio G.
    Liable-Sands, Louise M.
    Rheingold, Arnold L.
    [J]. ORGANIC LETTERS, 2008, 10 (20) : 4425 - 4428
  • [2] Effect of Linker Length on Selectivity and Cooperative Reactivity in Platinum-Catalyzed Asymmetric Alkylation of Bis(phenylphosphino)alkanes
    Anderson, Brian J.
    Reynolds, Samantha C.
    Guino-o, Marites A.
    Xu, Zhiming
    Glueck, David S.
    [J]. ACS CATALYSIS, 2016, 6 (12): : 8106 - 8114
  • [3] [Anonymous], DEPOSITION NUMBERS 2
  • [4] Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines
    Beaud, Rodolphe
    Phipps, Robert J.
    Gaunt, Matthew J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (40) : 13183 - 13186
  • [5] Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations
    Bhat, Vikram
    Welin, Eric R.
    Guo, Xuelei
    Stoltz, Brian M.
    [J]. CHEMICAL REVIEWS, 2017, 117 (05) : 4528 - 4561
  • [6] Blank N. F., J AM CHEM SOC
  • [7] Enantioselective synthesis of P-stereogenic benzophospholanes via palladium-catalyzed intramolecular cyclization
    Brunker, Tim J.
    Anderson, Brian J.
    Blank, Natalia F.
    Glueck, David S.
    Rheingold, Arnold L.
    [J]. ORGANIC LETTERS, 2007, 9 (06) : 1109 - 1112
  • [8] Pd-catalyzed dynamic kinetic enantioselective arylation of silylphosphines
    Chan, Vincent S.
    Bergman, Robert G.
    Toste, F. Dean
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) : 15122 - +
  • [9] Development of Ruthenium Catalysts for the Enantioselective Synthesis of P-Stereogenic Phosphines via Nucleophilic Phosphido Intermediates
    Chan, Vincent S.
    Chiu, Melanie
    Bergman, Robert G.
    Toste, F. Dean
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (16) : 6021 - 6032
  • [10] Asymmetric catalytic synthesis of P-stereogenic phosphines via a nucleophilic ruthenium phosphido complex
    Chan, VS
    Stewart, IC
    Bergman, RG
    Toste, FD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (09) : 2786 - 2787