Chiral Phosphoric Acid Catalyzed Asymmetric Synthesis of Axially Chiral Compounds†

被引:122
作者
Da, Bing-Chao [1 ,2 ]
Xiang, Shao-Hua [1 ,2 ,3 ]
Li, Shaoyu [1 ,2 ,3 ]
Tan, Bin [1 ,2 ]
机构
[1] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
[2] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Guangdong, Peoples R China
[3] Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518055, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
Axial chirality; Organocatalysis; Chiral phosphoric acid; Biaryls; Asymmetric synthesis; HIGHLY ATROPOSELECTIVE SYNTHESIS; NON-BIARYL ATROPISOMERS; BOND-FORMING REACTIONS; KINETIC RESOLUTION; RATIONAL DESIGN; BRONSTED ACIDS; CONSTRUCTION; ARYLATION; FUNCTIONALIZATION; 2-NAPHTHOLS;
D O I
10.1002/cjoc.202000751
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The well-defined conformational properties of axially chiral compounds bring extraordinary values to an assortment of bioactive molecules, advanced materials, organocatalysts as well as chiral ligands in asymmetric transformations. The demonstrated usefulness and untapped potential of axially chiral structural motifs stimulate increasing efforts to develop novel and efficient approaches for their preparation. In this regard, the chiral phosphoric acids broadly used in asymmetric Bronsted acid catalysis have shown high relevance for atroposelective synthesis as well. Our strong interest in reaction chemistry of atropisomers has established a rewarding research programme in our group. The course of studies will be recounted in this Account, with discussion focused on the use of chiral phosphoric acids to catalyze construction of several key axially chiral structures such as BINAM, BINOL, NOBIN, arylquinones, SPINOL, arylpyrrole analogues and axially chiral alkenes. What is the most favorite and original chemistry developed in your research group? Organocatalytic asymmetric arene C-H functionalization. What is the most important personality for scientific research? Persistence, smart thinking. What are your hobbies? Playing basketball, playing card. What's your favorite book(s)? The Ordinary World by the famous Chinese writer Yao Lu. Who influences you mostly in your life? My parents and my supervisors Prof. Guofu Zhong and Carlos F. Barbas III. How do you supervise your students? I advise my students to work smartly and work hard.
引用
收藏
页码:1787 / 1796
页数:10
相关论文
共 94 条
  • [1] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
    Akiyama, T
    Itoh, J
    Yokota, K
    Fuchibe, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
  • [2] Stronger bronsted acids
    Akiyama, Takahiko
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758
  • [3] Stronger Bronsted Acids: Recent Progress
    Akiyama, Takahiko
    Mori, Keiji
    [J]. CHEMICAL REVIEWS, 2015, 115 (17) : 9277 - 9306
  • [4] Approaching sub-ppm-level asymmetric organocatalysis of a highly challenging and scalable carbon-carbon bond forming reaction
    Bae, Han Yong
    Hoefler, Denis
    Kaib, Philip S. J.
    Kasaplar, Pinar
    De, Chandra Kanta
    Doehring, Arno
    Lee, Sunggi
    Kaupmees, Karl
    Leito, Ivo
    List, Benjamin
    [J]. NATURE CHEMISTRY, 2018, 10 (08) : 888 - 894
  • [5] Highly atroposelective synthesis of nonbiaryl naphthalene-1,2-diamine N-C atropisomers through direct enantioselective C-H amination
    Baig, He-Yuan
    Tan, Fu-Xin
    Liu, Tuan-Qing
    Zhu, Guo-Dong
    Tian, Jin-Miao
    Ding, Tong-Mei
    Chen, Zhi-Min
    Zhang, Shu-Yu
    [J]. NATURE COMMUNICATIONS, 2019, 10 (1)
  • [6] Chirally aminated 2-naphthols-organocatalytic synthesis of non-biaryl atropisomers by asymmetric Friedel-Crafts amination
    Brandes, S
    Bella, M
    Kjoersgaard, A
    Jorgensen, KA
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (07) : 1147 - 1151
  • [7] Non-biaryl atropisomers in organocatalysis
    Brandes, Sebastian
    Niess, Barbara
    Bella, Marco
    Prieto, Auxiliadora
    Overgaard, Jacob
    Jorgensen, Karl Anker
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (23) : 6039 - 6052
  • [8] Atroposelective synthesis of axially chiral biaryl compounds
    Bringmann, G
    Mortimer, AJP
    Keller, PA
    Gresser, MJ
    Garner, J
    Breuning, M
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) : 5384 - 5427
  • [9] Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products
    Bringmann, Gerhard
    Gulder, Tanja
    Gulder, Tobias A. M.
    Breuning, Matthias
    [J]. CHEMICAL REVIEWS, 2011, 111 (02) : 563 - 639
  • [10] Organocatalytic Enantioselective Synthesis of Atropisomeric Aryl-p-Quinones: Platform Molecules for Diversity-Oriented Synthesis of Biaryldiols
    Chen, Ye-Hui
    Li, Heng-Hui
    Zhang, Xiao
    Xiang, Shao-Hua
    Li, Shaoyu
    Tan, Bin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (28) : 11374 - 11378