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
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 20期
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
  • [21] Inverse-Electron-Demand Palladium-Catalyzed Asymmetric [4+2] Cycloadditions Enabled by Chiral P,S-Ligand and Hydrogen Bonding
    Wang, Ya-Ni
    Xiong, Qin
    Lu, Liang-Qiu
    Zhang, Qun-Liang
    Wang, Ying
    Lan, Yu
    Xiao, Wen-Jing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (32) : 11013 - 11017
  • [22] Enantioselective Synthesis of Oxazocines via MQ-Phos Enabled Palladium-Catalyzed Asymmetric Formal [4+4]-Cycloadditions
    Meng, Qiaojing
    Meng, Yinggao
    Liu, Qinglin
    Yu, Bing
    Li, Zhong-Jun
    Li, Er-Qing
    Zhang, Junliang
    ADVANCED SCIENCE, 2024,
  • [23] Asymmetric [2+1] cycloaddition of difluoroalkyl- substituted carbenes with alkenes under rhodium catalysis: Synthesis of chiral difluoroalkyl-substituted cyclopropanes
    Zhang, Xinyu
    Ning, Yongquan
    Tian, Chunqi
    Zanoni, Giuseppe
    Bi, Xihe
    ISCIENCE, 2023, 26 (03)
  • [24] Photocatalyzed [2+1] cyclization of alkenes and silylated trifluorodiazoethanes: facile entry into (difluoromethylene)cyclopropanes
    Chen, Suo
    Zhang, Yizhi
    Liu, Shanshan
    Shen, Xiao
    SCIENCE CHINA-CHEMISTRY, 2023, 66 (11) : 3141 - 3147
  • [25] Photocatalyzed [2+1] cyclization of alkenes and silylated trifluorodiazoethanes: facile entry into(difluoromethylene)cyclopropanes
    Suo Chen
    Yizhi Zhang
    Shanshan Liu
    Xiao Shen
    Science China(Chemistry), 2023, (11) : 3141 - 3147
  • [26] Photocatalyzed [2+1] cyclization of alkenes and silylated trifluorodiazoethanes: facile entry into(difluoromethylene)cyclopropanes
    Suo Chen
    Yizhi Zhang
    Shanshan Liu
    Xiao Shen
    Science China(Chemistry), 2023, 66 (11) : 3141 - 3147
  • [27] Photocatalyzed [2+1] cyclization of alkenes and silylated trifluorodiazoethanes: facile entry into (difluoromethylene)cyclopropanes
    Suo Chen
    Yizhi Zhang
    Shanshan Liu
    Xiao Shen
    Science China Chemistry, 2023, 66 : 3141 - 3147
  • [28] Copper-Catalyzed (2+1) Annulation of Acetophenones with Maleimides: Direct Synthesis of Cyclopropanes
    Manna, Srimanta
    Antonchick, Andrey P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (49) : 14845 - 14848
  • [29] Asymmetric [2+1]cycloaddition reactions of 1-seleno-2-silylethene
    Yamazaki, S
    Tanaka, M
    Yamabe, S
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (12): : 4046 - 4050
  • [30] Copper(I)-catalyzed asymmetric decarboxylative Mannich reaction enabled by acidic activation of 2H-azirines
    Hai-Jun Zhang
    Yan-Cheng Xie
    Liang Yin
    Nature Communications, 10
12345