Chirality Transfer and Memory of Chirality in Gold-Catalyzed Reactions

被引:90
|
作者
Patil, Nitin T. [1 ]
机构
[1] CSIR Indian Inst Chem Technol, CPC Div, Hyderabad 500607, Andhra Pradesh, India
关键词
chirality transfer; cyclization; gold; homogeneous catalysis; reaction mechanisms; ASYMMETRIC ALDOL REACTION; GOLD(I)-CATALYZED INTERMOLECULAR HYDROALKOXYLATION; INTRAMOLECULAR CARBOALKOXYLATION; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; PLATINUM CATALYSIS; ALPHA-AMINOALLENES; ALLYLIC ALCOHOLS; ALLENES;
D O I
10.1002/asia.201200194
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Over the last few years, gold-catalyzed reactions that involved chirality transfer and memory of chirality (MOC) have emerged as a powerful tool in enantioselective synthesis. This technique has allowed for the single-step synthesis of enantioenriched compounds from readily available starting materials. This Focus Review discusses this emerging field with an emphasis on mechanistic aspects and their applications in synthetic organic chemistry.
引用
收藏
页码:2186 / 2194
页数:9
相关论文
共 50 条
  • [1] Gold-catalyzed intramolecular hydroamination of allenes: a case of chirality transfer
    Patil, Nitin T.
    Lutete, Leopold Mpaka
    Nishina, Naoko
    Yamamoto, Yoshinori
    [J]. TETRAHEDRON LETTERS, 2006, 47 (27) : 4749 - 4751
  • [2] Gold-Catalyzed Synthesis of Chiral Cyclopentadienyl Esters via Chirality Transfer
    Zhao, Ke
    Hsu, Yu-Chen
    Yang, Ziguang
    Liu, Rai-Shung
    Zhang, Liming
    [J]. ORGANIC LETTERS, 2020, 22 (16) : 6500 - 6504
  • [3] Gold-catalyzed intermolecular hydroamination of allenes with arylamines and resulting high chirality transfer
    Nishina, Naoko
    Yamamoto, Yoshinori
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (20) : 3314 - 3317
  • [4] Chirality transfer in gold-catalyzed carbothiolation of o-alkynylphenyl 1-arylethyl sulfides
    Nakamura, Itaru
    Sato, Takuma
    Terada, Masahiro
    Yamamoto, Yoshinori
    [J]. ORGANIC LETTERS, 2008, 10 (13) : 2649 - 2651
  • [5] Gold-Catalyzed Carbene Transfer Reactions
    Shin, Seunghoon
    [J]. HOMOGENEOUS GOLD CATALYSIS, 2015, 357 : 25 - 62
  • [6] On the Memory of Chirality in Gold(I)-Catalyzed Intramolecular Carboalkoxylation of Alkynes
    Nieto Faza, Olalla
    Silva Lopez, Carlos
    de Lera, Angel R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10): : 3791 - 3796
  • [7] CHIRALITY TRANSFER IN PALLADIUM-CATALYZED REACTIONS OF ALLYLAMMONIUM SALTS
    DOI, T
    YANAGISAWA, A
    MIYAZAWA, M
    YAMAMOTO, K
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (02) : 389 - 392
  • [8] Transfer of Chirality for Memory and Separation
    Lauceri, Rosaria
    D'Urso, Alessandro
    Mammana, Angela
    Purrello, Roberto
    [J]. ELECTRONIC AND MAGNETIC PROPERTIES OF CHIRAL MOLECULES AND SUPRAMOLECULAR ARCHITECTURES, 2011, 298 : 143 - 188
  • [9] Efficient Synthesis of Enantioenriched Isoxazoles by Chirality Transfer in Gold-Catalyzed Cyclization/Methylene-Group Transfer Followed by Carbonyl Ene Reaction
    Gima, Shinya
    Nakamura, Itaru
    Terada, Masahiro
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (30) : 4375 - 4378
  • [10] Memory of chirality in reactions involving monoradicals
    Gloora, Christian Simon
    Denes, Fabrice
    Renaud, Philippe
    [J]. FREE RADICAL RESEARCH, 2016, 50 : S102 - S111