Merging of Palladium and Organocatalysis Enabled Asymmetric Decarboxylative (2+1) Cycloadditions toward Cyclopropanes

被引:0
|
作者
Yan, Biwei [1 ]
Ma, Pengchen [2 ,3 ]
Shu, Xiao [1 ]
Yin, Wenhao [1 ]
Guo, Wusheng [1 ]
机构
[1] Xi An Jiao Tong Univ, Frontier Inst Sci & Technol FIST, Xian 710049, Peoples R China
[2] Xi An Jiao Tong Univ, Minist Educ, Sch Chem, Xian Key Lab Sustainable Energy Mat Chem, Xian 710049, Peoples R China
[3] Xi An Jiao Tong Univ, Minist Educ, Engn Res Ctr Energy Storage Mat & Devices, Xian 710049, Peoples R China
关键词
C-BOND ACTIVATION; CATALYSIS; COMPLEXES; PK(A)S;
D O I
10.1021/acs.orglett.4c01088
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cascade reaction enabling enantio- and diastereoselective construction of strained cyclopropanes is described. This asymmetric (2+1) annulation process uses vinyl methylene carbonate and 2-cyanoacrylate as reaction partners in the presence of Pd(PPh3)(4) as a precatalyst and an enantioenriched phosphoramidite ligand featuring a morpholine functionality. Mechanistic investigations unveil that the PPh3 derived from the Pd(PPh3)(4) and the morpholine-containing phosphoramidite work as cooperative phosphorus and Br & oslash;nsted base catalysts to promote the reaction.
引用
收藏
页码:4274 / 4279
页数:6
相关论文
共 50 条
  • [1] Decarboxylative [4+2] Cycloaddition by Synergistic Palladium and Organocatalysis
    Leth, Lars A.
    Glaus, Florian
    Meazza, Marta
    Fu, Liang
    Thogersen, Mathias K.
    Bitsch, Emma A.
    Jorgensen, Karl Anker
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (49) : 15272 - 15276
  • [2] P,SLigands for the Asymmetric Construction of Quaternary Stereocenters in Palladium-Catalyzed Decarboxylative [4+2] Cycloadditions
    Wei, Yi
    Lu, Liang-Qiu
    Li, Tian-Ren
    Feng, Bin
    Wang, Qiang
    Xiao, Wen-Jing
    Alper, Howard
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (06) : 2200 - 2204
  • [3] The synthesis of tetracyclic coumarins via decarboxylative asymmetric [4+2] cycloadditions enabled by Pd(0)/Cu(I) synergistic catalysis
    Wang, Kai
    Lin, Xiangfeng
    Li, Qian
    Liu, Yan
    Li, Can
    CHINESE JOURNAL OF CATALYSIS, 2022, 43 (07) : 1812 - 1817
  • [5] Palladium-Catalyzed [2+1] Cycloadditions Affording Vinylidenecyclopropanes as Precursors of 7-Membered Carbocycles
    Lepronier, Aymeric
    Achard, Thierry
    Giordano, Laurent
    Tenaglia, Alphonse
    Buono, Gerard
    Clavier, Herve
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (04) : 631 - 642
  • [6] [2+1] cycloadditions of terminal alkynes to norbornene derivatives catalyzed by palladium complexes with phosphinous acid ligands
    Bigeault, J
    Giordano, L
    Buono, G
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (30) : 4753 - 4757
  • [7] Asymmetric [3+2] Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Aldehydes by Synergistic Palladium and Organocatalysis
    Halskov, Kim Soholm
    Naesborg, Line
    Tur, Fernando
    Jorgensen, Karl Anker
    ORGANIC LETTERS, 2016, 18 (09) : 2220 - 2223
  • [8] Lewis Acid-Enabled Chemodivergent Cycloadditions of Donor-Acceptor Cyclopropanes with Indoline-2-Thiones
    Zhai, Chen-Ying
    Zhao, Bing
    Wang, Xue-Long
    Liu, Huai-Yan
    Zhao, Bo
    Jiang, Yan
    JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (09): : 3209 - 3222
  • [9] Enantiodivergent Synthesis of Tertiary α-Aryl 1-Indanones: Evidence Toward Disparate Mechanisms in the Palladium-Catalyzed Decarboxylative Asymmetric Protonation
    Kingston, Cian
    Guiry, Patrick J.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (07): : 3806 - 3819
  • [10] Intramolecular photochemical [2+1]-cycloadditions of nucleophilic siloxy carbenes
    Bunyamin, Amanda
    Hua, Carol
    Polyzos, Anastasios
    Priebbenow, Daniel L.
    CHEMICAL SCIENCE, 2022, 13 (11) : 3273 - 3280