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

被引:13
|
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
  • [1] Rhodium-Catalyzed Chemodivergent Regio- and Enantioselective Allylic Alkylation of Indoles
    Sun, Minghe
    Liu, Min
    Li, Changkun
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (10) : 3457 - 3462
  • [2] Regio- and Enantioselective Rhodium-Catalyzed Allylic Alkylation of Racemic Allylic Alcohols with 1,3-Diketones
    Tang, Sheng-Biao
    Zhang, Xiao
    Tu, Hang-Fei
    You, Shu-Li
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (24) : 7737 - 7742
  • [3] Rhodium-Catalyzed Regio- and Enantioselective Allylic Sulfonylation from Sulfonyl Hydrazides
    Rehman, Sajid Ur
    Li, Changkun
    ORGANIC LETTERS, 2023, 25 (20) : 3693 - 3697
  • [4] Rhodium-Catalyzed Branched and Enantioselective Direct α-Allylic Alkylation of Simple Ketones with Alkynes
    Xie, Liyu
    Yang, Haijian
    Ma, Mingliang
    Xing, Dong
    ORGANIC LETTERS, 2020, 22 (05) : 2007 - 2011
  • [5] Regio- and enantiospecific rhodium-catalyzed allylic alkylation reactions using copper(I) enolates
    Leahy, DK
    Evans, PA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U316 - U316
  • [6] Rhodium-Catalyzed Regio- and Enantioselective Allylic Amination of Racemic 1,2-Disubstituted Allylic Phosphates
    Xu, Wen-Bin
    Sun, Minghe
    Shu, Mouhai
    Li, Changkun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (22) : 8255 - 8260
  • [7] Regio- and diastereoselective tandem rhodium-catalyzed allylic alkylation Pauson-Khand annulation reactions
    Evans, PA
    Robinson, JE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) : 4609 - 4610
  • [8] Regio- and stereoselective rhodium-catalyzed allylic alkylations of chelated enolates
    Kazmaier, Uli
    Stolz, Daniel
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) : 3072 - 3075
  • [9] Cobalt-Catalyzed Regio- and Enantioselective Allylic Alkylation of Malononitriles
    Ghorai, Samir
    Rehman, Sajid Ur
    Xu, Wen-Bin
    Huang, Wen-Yu
    Li, Changkun
    ORGANIC LETTERS, 2020, 22 (09) : 3519 - 3523
  • [10] Rhodium-catalyzed regio- and stereoselective addition of diphenylphosphine oxide to alkynes
    Han, LB
    Zhao, CQ
    Tanaka, M
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17): : 5929 - 5932