Enantioselective decarboxylative protonation and deuteration of β-ketocarboxylic acids

被引:10
|
作者
Mizutani, Haruna [1 ]
Kawanishi, Ryouta [1 ]
Shibatomi, Kazutaka [1 ]
机构
[1] Toyohashi Univ Technol, Dept Appl Chem & Life Sci, 1-1 Hibarigaaka,Tempaku Cho, Toyohashi, Aichi 4418580, Japan
关键词
DERIVATIVES; ENANTIOMERS;
D O I
10.1039/d1cc01610e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantioselective decarboxylative protonation of tetralone-derived beta-ketocarboxylic acids was achieved with up to 89% enantiomeric excess (ee)-in the presence of a chiral primary amine catalyst. Furthermore, this method was applied to enantioselective deuteration to afford the corresponding alpha-deuterioketones with up to 88% ee.
引用
收藏
页码:6676 / 6679
页数:4
相关论文
共 50 条
  • [21] On the Protonation and Deuteration of Simple Phenols
    Hartmann, Horst
    Yu, Xiuling
    CHEMISTRYSELECT, 2022, 7 (22):
  • [22] Protonation, deuteration, and formylation of aceperidazylenes
    Mezheritskii, V. V.
    Minyaeva, L. G.
    Omelichkin, N. I.
    Milov, A. A.
    Lysenko, K. A.
    Smolyakov, A. F.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (07) : 1022 - 1027
  • [23] Protonation, deuteration, and formylation of aceperidazylenes
    V. V. Mezheritskii
    L. G. Minyaeva
    N. I. Omelichkin
    A. A. Milov
    K. A. Lysenko
    A. F. Smolyakov
    Russian Journal of Organic Chemistry, 2014, 50 : 1022 - 1027
  • [24] Selective Copper- or Silver-Catalyzed Decarboxylative Deuteration of Aromatic Carboxylic Acids
    Rudzki, Martin
    Alcalde-Aragones, Ana
    Dzik, Wojciech I.
    Rodriguez, Nuria
    Goossen, Lukas J.
    SYNTHESIS-STUTTGART, 2012, 44 (02): : 184 - 193
  • [25] Organocatalytic Enantioselective Decarboxylative Protonation Reaction of Meldrum's Acid Derivatives under PTC Conditions
    Legros, Fabien
    Martzel, Thomas
    Briere, Jean-Francois
    Oudeyer, Sylvain
    Levacher, Vincent
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (17) : 1975 - 1983
  • [26] Rhodium-Catalyzed Enantioselective Decarboxylative Alkynylation of Allenes with Arylpropiolic Acids
    Grugel, Christian P.
    Breit, Bernhard
    ORGANIC LETTERS, 2018, 20 (04) : 1066 - 1069
  • [27] Organocatalytic Enantioselective Decarboxylative Addition of Malonic Acids Half Thioesters to Isatins
    Hara, Noriyuki
    Nakamura, Shuichi
    Funahashi, Yasuhiro
    Shibata, Norio
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) : 2976 - 2980
  • [28] Organocatalytic Enantioselective Decarboxylative Michael Addition of β-Keto Acids to Dicyanoolefins and Disulfonylolefins
    Wei, Yi
    Guo, Ran
    Dang, Yanfeng
    Nie, Jing
    Ma, Jun-An
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (17) : 2721 - 2726
  • [29] Catalyst-free decarboxylative deuteration using tailored photoredox-active carboxylic acids
    Liu, Shuai
    Liao, Hongze
    Chen, Bin
    Guo, Tengyu
    Zhang, Zhizhen
    Lin, Houwen
    GREEN CHEMISTRY, 2024, 26 (20) : 10456 - 10462
  • [30] Enantioselective protonation
    Mohr, Justin T.
    Hong, Allen Y.
    Stoltz, Brian M.
    NATURE CHEMISTRY, 2009, 1 (05) : 359 - 369