Atroposelective Synthesis of Axially Chiral All-Benzenoid Biaryls by the Gold-Catalyzed Intramolecular Hydroarylation of Alkynones

被引：35
作者：
Satoh, Masakazu [1 ]
Shibata, Yu [1 ]
Kimura, Yuki [1 ]
Tanaka, Ken [1 ]
机构：
[1] Tokyo Inst Technol, Dept Chem Sci & Engn, Meguro Ku, Tokyo 1528550, Japan
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 26期
基金：
日本学术振兴会; 日本科学技术振兴机构;
关键词：
Asymmetric catalysis; Homogeneous catalysis; Gold; Hydroarylation; Alkynes; Biaryls; ENANTIOSELECTIVE 2+2+2 CYCLOADDITION; CROSS-CYCLOTRIMERIZATION; ASYMMETRIC-SYNTHESIS; ALKYNES; CYCLOISOMERIZATION; CONSTRUCTION; COMPLEXES; HETEROCYCLES; 2-NAPHTHOLS; DERIVATIVES;
D O I：
10.1002/ejoc.201600834
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The cationic gold(I)/(R)-xyl-binap complex was shown to catalyze the atroposelective intramolecular hydroarylation of alkynones to produce enantioenriched axially chiral all-benzenoid biaryls, 4-aryl-2-naphthol derivatives, with up to 67%ee. The reaction of a racemic alkynone in the presence of the same gold(I) catalyst also afforded the corresponding axially chiral all-benzenoid biaryl in excellent yield with 70%ee.
引用
收藏
页码：4465 / 4469
页数：5
相关论文
共 87 条
  • [1] Recent Advances in Stereoselective [2+2+2] Cycloadditions
    Amatore, Muriel
    Aubert, Corinne
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (02) : 265 - 286
  • [2] Double-Stereodifferentiation in Rhodium-Catalyzed [2+2+2] Cycloaddition: Chiral Ligand/Chiral Counterion Matched Pair
    Auge, Mylene
    Feraldi-Xypolia, Alexandra
    Barbazanges, Marion
    Aubert, Corinne
    Fensterbank, Louis
    Gandon, Vincent
    Kolodziej, Emilie
    Ollivier, Cyril
    [J]. ORGANIC LETTERS, 2015, 17 (15) : 3754 - 3757
  • [3] Atroposelective [2+2+2] cycloadditions catalyzed by a rhodium(I)-chiral phosphate system
    Auge, Mylene
    Barbazanges, Marion
    Anh Tuan Tran
    Simonneau, Antoine
    Elley, Paulin
    Amouri, Hani
    Aubert, Corinne
    Fensterbank, Louis
    Gandon, Vincent
    Malacria, Max
    Moussa, Jamal
    Ollivier, Cyril
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (71) : 7833 - 7835
  • [4] The asymmetric Suzuki coupling route to axially chiral biaryls
    Baudoin, O
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (20) : 4223 - 4229
  • [5] Organocatalytic Strategies for the Synthesis of Axially Chiral Compounds
    Bencivenni, Giorgio
    [J]. SYNLETT, 2015, 26 (14) : 1915 - 1922
  • [6] Alkenylation of Arenes and Heteroarenes with Alkynes
    Boyarskiy, Vadim P.
    Ryabukhin, Dmitry S.
    Bokach, Nadezhda A.
    Vasilyev, Aleksander V.
    [J]. CHEMICAL REVIEWS, 2016, 116 (10) : 5894 - 5986
  • [7] 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
  • [8] Bringmann G., 2005, ANGEW CHEM INT EDIT, V117, P5518, DOI 10.1002/ange.200462661
  • [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] de Haro T., 2014, Comprehensive Organic Synthesis, V2nd ed., P1621
123456789