Organocatalytic Dearomatization of β-Naphthols through a 1,6-Conjugated Addition of Alkynyl 7-Methylene-7H-indoles Formed In Situ

被引：0
作者：
Kang, Shengfu [1 ]
Liu, Xiaohong [1 ]
Zhang, Yi [1 ]
Fang, Fang [2 ]
Li, Wenjun [1 ]
Li, Pengfei [2 ]
机构：
[1] Qingdao Univ, Sch Pharm, Dept Med Chem, Qingdao 266021, Shandong, Peoples R China
[2] Southern Univ Sci & Technol SUSTech, Coll Sci, Guangming Adv Res Inst, Dept Chem,Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2025年 / 367卷 / 01期
关键词：
Addition; Allenes; Dearomatization; Indolylmethanol; Organocatalysis; CATALYTIC ASYMMETRIC DEAROMATIZATION; ENANTIOSELECTIVE SYNTHESIS; METAL CATALYSIS; ACID; CONSTRUCTION; ALLENES; REGIO;
D O I：
10.1002/adsc.202401173
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Organocatalytic dearomatization of beta-naphthols has been achieved via a 1,6-conjugated addition of 2-naphthols to alkynyl 7-methylene-7H-indoles in situ generated from alpha-(7-indolyl)methanols. In the presence of racemic phosphoric acid, a series of tetrasubstituted allenes was obtained in high yields. Particularly, with the aid of chiral phosphoric acid, asymmetric dearomatization of beta-naphthols was investigated, affording axially chiral tetrasubstituted allenes with moderate enantioselectivity.
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页数：6
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共 57 条
  • [1] Stronger bronsted acids
    Akiyama, Takahiko
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758
  • [2] Recent Advances in the Catalytic Dearomatization of Naphthols
    An, Juzeng
    Bandini, Marco
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (27) : 4087 - 4097
  • [3] Highly Enantioselective Alkylation Reaction of Enamides by Bronsted-Acid Catalysis
    Guo, Qi-Xiang
    Peng, Yun-Gui
    Zhang, Jin-Wei
    Song, Liu
    Feng, Zhang
    Gong, Liu-Zhu
    [J]. ORGANIC LETTERS, 2009, 11 (20) : 4620 - 4623
  • [4] Lewis Acid Catalyzed Intramolecular Direct Ene Reaction of Indoles
    Han, Bo
    Xiao, You-Cai
    Yao, Yuan
    Chen, Ying-Chun
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (52) : 10189 - 10191
  • [5] Catalytic Asymmetric Allylic Substitution/Isomerization with Central Chirality Transposition
    Han, Zhengyu
    Zhuang, Han
    Tang, Luning
    Zang, Yu
    Guo, Wengang
    Huang, Hai
    Sun, Jianwei
    [J]. ORGANIC LETTERS, 2022, 24 (23) : 4246 - 4251
  • [6] Alienation of Terminal Alkynes with Aldehydes and Ketones
    Huang, Xin
    Ma, Shengming
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2019, 52 (05) : 1301 - 1312
  • [7] Organocatalytic Enantioselective Aza-Michael Addition of Arylamines to 7-Methide-7H-Indoles
    Li, Fushuai
    Yang, Zhihong
    Yang, Yanyan
    Huang, Qiuhong
    Chen, Xuling
    Li, Pengfei
    Dong, Mingxin
    Li, Wenjun
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (10) : 2557 - 2561
  • [8] Asymmetric Arylative Dearomatization of b-Naphthols Catalyzed by a Chiral Phosphoric Acid
    Li, Xiao-Qiang
    Yang, Hui
    Wang, Jiao-Jiao
    Gou, Bo-Bo
    Chen, Jie
    Zhou, Ling
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (22) : 5381 - 5385
  • [9] Catalytic enantioselective synthesis of chiral tetraarylmethanes
    Li, Xingguang
    Duan, Meng
    Deng, Zhiqin
    Shao, Qianzhen
    Chen, Min
    Zhu, Guangyu
    Houk, K. N.
    Sun, Jianwei
    [J]. NATURE CATALYSIS, 2020, 3 (12) : 1010 - 1019
  • [10] Organocatalytic Enantioselective Synthesis of Chiral Allenes: Remote Asymmetric 1,8-Addition of Indole Imine Methides
    Li, Xingguang
    Sun, Jianwei
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (39) : 17049 - 17054
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