Chirality transfer in gold-catalyzed carbothiolation of o-alkynylphenyl 1-arylethyl sulfides

被引:117
|
作者
Nakamura, Itaru [1 ]
Sato, Takuma [1 ]
Terada, Masahiro [1 ]
Yamamoto, Yoshinori [1 ]
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1021/ol8007556
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chirality transfer in gold-catalyzed carbothiolation of o-alkynylphenyl 1-arylethyl sulfides 1 proceeded with retention of the configuration at the 1-arylethyl group. This result suggests that the [1,3] migration of 1-arylethyl group proceeds through formation of the contact ion pair B followed by C-C bond formation.
引用
收藏
页码:2649 / 2651
页数:3
相关论文
共 41 条
  • [1] Chirality Transfer and Memory of Chirality in Gold-Catalyzed Reactions
    Patil, Nitin T.
    CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (10) : 2186 - 2194
  • [2] Gold-catalyzed intramolecular hydroamination of allenes: a case of chirality transfer
    Patil, Nitin T.
    Lutete, Leopold Mpaka
    Nishina, Naoko
    Yamamoto, Yoshinori
    TETRAHEDRON LETTERS, 2006, 47 (27) : 4749 - 4751
  • [3] Gold-Catalyzed Bicyclic Annulations of N-(o-Alkynylphenyl)imines with α-Diazo Esters to Form 5,6-Dihydroindolo[2,1-a]isoquinolines
    Narode, Akshay Subhash
    Liu, Rai-Shung
    ORGANIC LETTERS, 2022, 24 (11) : 2165 - 2169
  • [4] Gold-Catalyzed Synthesis of Chiral Cyclopentadienyl Esters via Chirality Transfer
    Zhao, Ke
    Hsu, Yu-Chen
    Yang, Ziguang
    Liu, Rai-Shung
    Zhang, Liming
    ORGANIC LETTERS, 2020, 22 (16) : 6500 - 6504
  • [5] Gold-catalyzed intermolecular hydroamination of allenes with arylamines and resulting high chirality transfer
    Nishina, Naoko
    Yamamoto, Yoshinori
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (20) : 3314 - 3317
  • [6] Sequential Gold-Catalyzed Carbene Transfer/Ring Closure: Oxidative Cyclization of β-(2-Alkynylphenyl)-α,β-ynones to Indenofuranones
    Rode, Navnath
    Marinelli, Fabio
    Arcadi, Antonio
    Adak, Tapas
    Rudolph, Matthias
    Rominger, Frank
    Hashmi, A. Stephen K.
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (24) : 4790 - 4794
  • [7] Gold-catalyzed intramolecular carbothiolation of alkynes:: Synthesis of 2,3-disubstituted benzothiophenes from (α-alkoxy alkyl) (ortho-alkynyl phenyl) sulfides
    Nakamura, Itaru
    Sato, Takuma
    Yamamoto, Yoshinori
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (27) : 4473 - 4475
  • [8] Gold-Catalyzed Cyclization and Subsequent Arylidene Group Transfer of O-Propioloyl Oximes
    Nakamura, Itaru
    Okamoto, Masashi
    Terada, Masahiro
    ORGANIC LETTERS, 2010, 12 (11) : 2453 - 2455
  • [9] 1,6-Carbene Transfer: Gold-Catalyzed Oxidative Diyne Cyclizations
    Noesel, Pascal
    Comprido, Laura Nunes dos Santos
    Lauterbach, Tobias
    Rudolph, Matthias
    Rominger, Frank
    Hashmi, A. Stephen K.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (41) : 15662 - 15666
  • [10] 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
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (30) : 4375 - 4378