Asymmetric Dearomatization of Indole by Palladium/PC-Phos-Catalyzed Dynamic Kinetic Transformation

被引：58
作者：
Chu, Haoke [1 ]
Cheng, Jie [2 ]
Yang, Junfeng [1 ]
Guo, Yin-Long [2 ]
Zhang, Junliang [1 ]
机构：
[1] Fudan Univ, Dept Chem, 2005 Songhu Rd, Shanghai, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Stake Key Lab Organometall Chem, Shanghai, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 49期
关键词：
alkynes; catalytic asymmetric dearomatization; chiral spiroindolenine; dynamic kinetic transformation; palladium; ENANTIOSELECTIVE CONSTRUCTION; ALLYLIC DEAROMATIZATION; SPIROCYCLIC OXINDOLES; HIGHLY EFFICIENT; CASCADE; REDUCTION; ACCESS; SPIROINDOLENINES; CYCLOADDITIONS; RACEMIZATION;
D O I：
10.1002/anie.202010164
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A palladium-catalyzed intermolecular dynamic kinetic asymmetric dearomatization of 3-arylindoles with internal alkynes was developed with the use of achiral Xantphos and chiral sulfinamide phosphine ligand (PC-Phos) as the co-ligands. This method could deliver various spiro[indene-1,3 '-indole] compounds in good yields (up to 95 % yield) with up to 98 % ee. The salient features of the transformation include the use of readily available substrates, ease of scale-up and the versatile functionalization of the products. The mechanistic experiments gave some insights on active intermediates.
引用
收藏
页码：21991 / 21996
页数：6
相关论文
共 87 条
  • [41] Enantioselective construction of spirocyclic oxindolic Cyclopentanes by palladium-catalyzed trimethylenemethane-[3+2]-cycloaddition
    Trost, Barry M.
    Cramer, Nicolai
    Silverman, Steven M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) : 12396 - +
  • [42] Trost BM, 2007, ALDRICHIM ACTA, V40, P59
  • [43] An Organocatalytic [3+2] Cyclisation Strategy for the Highly Enantioselective Synthesis of Spirooxindoles
    Voituriez, Arnaud
    Pinto, Nathalie
    Neel, Mathilde
    Retailleau, Pascal
    Marinetti, Angela
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (42) : 12541 - 12544
  • [44] Wang, 2017, ANGEW CHEM, V129, P15289
  • [45] Wang L., 2017, ANGEW CHEM, V129, P8636, DOI DOI 10.1002/ANIE.201900600
  • [46] Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications
    Wang, Lei
    Chen, Mingjie
    Zhang, Peichao
    Li, Wenbo
    Zhang, Junliang
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (09) : 3467 - 3473
  • [47] Switchable Access to Different Spirocyclopentane Oxindoles by N-Heterocyclic Carbene Catalyzed Reactions of Isatin-Derived Enals and N-Sulfonyl Ketimines
    Wang, Lei
    Li, Sun
    Bluemel, Marcus
    Puttreddy, Rakesh
    Peuronen, Anssi
    Rissanen, Kari
    Enders, Dieter
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (29) : 8516 - 8521
  • [48] Wang Y., 2017, ANGEW CHEM, V129, P16121
  • [49] Iridium-Catalyzed Asymmetric Allylic Dearomatization by a Desymmetrization Strategy
    Wang, Ye
    Zheng, Chao
    You, Shu-Li
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (47) : 15093 - 15097
  • [50] Ming-Phos/Gold(I)-Catalyzed Diastereo- and Enantioselective Synthesis of Indolyl-Substituted Cyclopenta[c]furans
    Wang, Yidong
    Zhang, Zhan-Ming
    Liu, Feng
    He, Yinyan
    Zhang, Junhang
    [J]. ORGANIC LETTERS, 2018, 20 (20) : 6403 - 6406
123456789