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
  • [1] Highly Enantioselective Control of Dynamic Cascade Transformations by Dual Catalysis: Asymmetric Synthesis of Polysubstituted Spirocyclic Oxindoles
    Afewerki, Samson
    Ma, Guangning
    Ibrahem, Ismail
    Liu, Leifeng
    Sun, Junliang
    Cordova, Armando
    [J]. ACS CATALYSIS, 2015, 5 (02): : 1266 - 1272
  • [2] Formation of palladium(0) complexes from Pd(OAc)2 and a bidentate phosphine ligand (dppp) and their reactivity in oxidative addition
    Amatore, C
    Jutand, A
    Thuilliez, A
    [J]. ORGANOMETALLICS, 2001, 20 (15) : 3241 - 3249
  • [3] Kinetic Data on the Synergetic Role of Amines and Water in the Reduction of Phosphine-Ligated Palladium(II) to Palladium(0)
    Amatore, Christian
    El Kaim, Laurent
    Grimaud, Laurence
    Jutand, Anny
    Meignie, Alice
    Romanov, Georgy
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (22) : 4709 - 4713
  • [4] [Anonymous], 2017, ANGEW CHEM
  • [5] [Anonymous], 2016, ANGEW CHEM-GER EDIT
  • [6] Bai L., 2018, ANGEW CHEM, V130, P5245
  • [7] Palladium/Norbornene-Catalyzed C-H Alkylation/Alkyne Insertion/Indole Dearomatization Domino Reaction: Assembly of Spiroindolenine-Containing Pentacyclic Frameworks
    Bai, Lu
    Liu, Jingjing
    Hu, Wenjie
    Li, Kunyu
    Wang, Yaoyu
    Luan, Xinjun
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (18) : 5151 - 5155
  • [8] Ball -Jones N. R., 2014, ANGEW CHEM, V126, P9616
  • [9] Catalytic Enantioselective Carboannulation with Allylsilanes
    Ball-Jones, Nicolas R.
    Badillo, Joseph J.
    Tran, Ngon T.
    Franz, Annaliese K.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) : 9462 - 9465
  • [10] Oxidative N-Heterocyclic Carbene Catalyzed Dearomatization of Indoles to Spirocyclic Indolenines with a Quaternary Carbon Stereocenter
    Bera, Srikrishna
    Daniliuc, Constantin G.
    Studer, Armido
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (26) : 7402 - 7406
123456789