Nickel-catalysed enantioselective reaction of secondary phosphine oxides and activated vinylcyclopropanes

被引:13
|
作者
Huang, Zhuo [1 ]
Liu, Xu-Teng [1 ]
Cui, Ranran [1 ]
Zhang, Qing-Wei [1 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Key Lab Precis & Intelligent Chem, Hefei 230026, Peoples R China
关键词
VINYL-CYCLOPROPANES; 3+2 CYCLOADDITION; ASYMMETRIC-SYNTHESIS; LIGANDS; ARYLATION; BORANES; RINGS;
D O I
10.1039/d3ob00389b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Activated vinylcyclopropanes can form zwitterionic pi-allylmetal species in the presence of transition metals and are widely used in organic synthesis. A nickel-catalyzed asymmetric allylation of secondary phosphine oxides with vinylcyclopropanes was described. Tertiary phosphine oxide products could be obtained with up to 91% yield and 92% ee.
引用
收藏
页码:3096 / 3100
页数:5
相关论文
共 50 条
  • [31] Cyclopropane formation by nickel-catalysed electroreductive coupling of activated olefins and unactivated gem-dibromo compounds
    Sengmany, S
    Léonel, E
    Paugam, JP
    Nédélec, JY
    TETRAHEDRON, 2002, 58 (02) : 271 - 277
  • [32] Thermal stability of primary and secondary phosphine oxides formed as a reaction of phosphine oxide with ketones
    Gorbachuk, E. V.
    Badeeva, E. K.
    Katsyuba, S. A.
    Pavlov, P. O.
    Khayarov, Kh. R.
    Sinyashin, O. G.
    Yakhvarov, D. G.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2016, 191 (11-12) : 1480 - 1481
  • [33] Enantioselective chlorinative aldol reaction of α-substituted acroleins catalyzed by chiral phosphine oxides
    Kotani, Shunsuke
    Hanamure, Takuya
    Nozaki, Hirono
    Sugiura, Masaharu
    Nakajima, Makoto
    TETRAHEDRON-ASYMMETRY, 2017, 28 (02) : 282 - 287
  • [34] Palladium catalysed enantioselective phosphination reactions using secondary phosphine-boranes and aryl iodide
    Pican, P
    Gaumont, AC
    CHEMICAL COMMUNICATIONS, 2005, (18) : 2393 - 2395
  • [35] Nickel-catalysed asymmetric hydromonofluoromethylation of 1,3-enynes for enantioselective construction of monofluoromethyl-tethered chiral allenes
    Zhang, Ying
    Yang, Jimin
    Ruan, Yu-Long
    Liao, Ling
    Ma, Chuang
    Xue, Xiao-Song
    Yu, Jin-Sheng
    CHEMICAL SCIENCE, 2023, 14 (44) : 12676 - 12683
  • [36] Enantioselective Reaction of N-Unprotected Activated Ketimines with Phosphine Oxides Catalyzed by Chiral Imidazoline-Phosphoric Acids br
    Ogura, Kazuki
    Isozumi, Itsuki
    Takehara, Tsunayoshi
    Suzuki, Takeyuki
    Nakamura, Shuichi
    ORGANIC LETTERS, 2022, : 8088 - 8092
  • [37] Unsymmetric N-heterocyclic carbene ligand enabled nickel-catalysed arylation of bulky primary and secondary amines
    Wang, Zi-Chao
    Li, Yan-Yu
    Zhang, Shuo-Qing
    Hong, Xin
    Shi, Shi-Liang
    CHEMICAL SCIENCE, 2023, 14 (16) : 4390 - 4396
  • [38] Sequential olefination-dimerisation of benzylic dithioacetals by the nickel-catalysed reaction with methyl Grignard or zinc reagent
    Yu, Lei
    Lai, Guo-Qiao
    Zhang, Pinglu
    Li, Ze
    Luh, Tien-Yau
    RSC ADVANCES, 2022, 12 (16) : 9653 - 9659
  • [39] Chiral 1,1′-Bi(tetrahydroisoquinoline)-Type Diamines as Efficient Ligands for Nickel-Catalysed Enantioselective Michael Addition to Nitroalkenes
    Wilckens, Kristina
    Duhs, Marcel-Antoine
    Lentz, Dieter
    Czekelius, Constantin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (28) : 5441 - 5446
  • [40] Enantioselective catalysis XVI: regio- and enantioselectivity in nickel-catalysed cross-coupling reactions of allylic substrates with Grignard reagents
    Nagel, U
    Nedden, HG
    INORGANICA CHIMICA ACTA, 1998, 269 (01) : 34 - 42