Rhodium-catalyzed regio- and enantioselective allylic alkylation of pyrazol-5-ones with alkynes

被引:15
|
作者
Ji, Ding-Wei [1 ,2 ]
Yang, Fan [1 ]
Chen, Bing-Zhi [1 ,2 ]
Min, Xiang-Ting [1 ,2 ]
Kuai, Chang-Sheng [1 ]
Hu, Yan-Cheng [1 ]
Chen, Qing-An [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
C-C; PRIMARY ALCOHOLS; TERMINAL ALKYNES; PALLADIUM; ALLYLATION; ACID; REGIOSELECTIVITY; HYDROAMINATION; INDOLES; KETONES;
D O I
10.1039/d0cc04002a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A rhodium-catalyzed asymmetric allylic alkylation of pyrazol-5-ones with internal alkynes is illustrated. In the presence of a chiral rhodium-hydride catalyst, functionalized heterocyclic products bearing an all-carbon quaternary stereogenic center were obtained in high yields with satisfactory enantioselectivities. This protocol also features good regiocontrol and a high atom economy without stoichiometric by-product formation.
引用
收藏
页码:8468 / 8471
页数:4
相关论文
共 50 条
  • [21] Rhodium-Catalyzed Enantioselective Intermolecular Hydroalkoxylation of Allenes and Alkynes with Alcohols: Synthesis of Branched Allylic Ethers
    Liu, Zi
    Breit, Bernhard
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (29) : 8440 - 8443
  • [22] Rhodium-Catalyzed Chemo-, Regio-, and Enantioselective Allylation of 2-Aminothiazoles with Terminal Allenes
    Zheng, Jun
    Woerl, Benjamin
    Breit, Bernhard
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (31-32) : 5180 - 5182
  • [23] Rhodium-Catalyzed Enantioselective Isomerization of Secondary Allylic Alcohols
    Liu, Tang-Lin
    Ng, Teng Wei
    Zhao, Yu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (10) : 3643 - 3646
  • [24] Pd-Catalyzed Asymmetric Allylic Alkylation of Pyrazol-5-ones with Allylic Alcohols: The Role of the Chiral Phosphoric Acid in C-O Bond Cleavage and Stereocontrol
    Tao, Zhong-Lin
    Zhang, Wen-Quan
    Chen, Dian-Feng
    Adele, Arafate
    Gong, Liu-Zhu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (25) : 9255 - 9258
  • [25] Regio- and Enantioselective Synthesis of Chiral Pyrimidine Acyclic Nucleosides via Rhodium-Catalyzed Asymmetric Allylation of Pyrimidines
    Liang, Lei
    Xie, Ming-Sheng
    Qin, Tao
    Zhu, Man
    Qu, Gui-Rong
    Guo, Hai-Ming
    ORGANIC LETTERS, 2017, 19 (19) : 5212 - 5215
  • [26] Palladium-catalyzed Regio- and Diastereoselective Allylic Alkylation in Ionic Liquids
    Kawatsura, Motoi
    Nobuto, Hideyuki
    Hayashi, Shunsuke
    Hirakawa, Takuya
    Ikeda, Daiji
    Itoh, Toshiyuki
    CHEMISTRY LETTERS, 2011, 40 (09) : 953 - 955
  • [27] Ruthenium-Catalyzed Regio- and Enantioselective Allylic Substitution with Water: Direct Synthesis of Chiral Allylic Alcohols
    Kanbayashi, Naoya
    Onitsuka, Kiyotaka
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (22) : 5197 - 5199
  • [28] Rhodium-Catalyzed Asymmetric Allylic Dearomatization of β-Naphthols: Enantioselective Control of Prochiral Nucleophiles
    Tang, Sheng-Biao
    Tu, Hang-Fei
    Zhang, Xiao
    You, Shu-Li
    ORGANIC LETTERS, 2019, 21 (15) : 6130 - 6134
  • [29] Rhodium-Catalyzed Regio- and Diastereoselective Hydroarylation of Allenes: An Unprecedented Ene Reaction
    Ghazvini, Helya J.
    Khosravi, Hormoz
    Mirzaei, Saber
    Balalaie, Saeed
    Breit, Bernhard
    ACS CATALYSIS, 2021, 11 (23) : 14570 - 14574
  • [30] Rhodium-Catalyzed Regio- and Stereoselective [2+2] Cycloaddition of Allenamides
    Zheng, Wei-Feng
    Bora, Pranjal Protim
    Sun, Gui-Jun
    Kang, Qiang
    ORGANIC LETTERS, 2016, 18 (15) : 3694 - 3697