Asymmetric Michael Reaction Catalyzed by Proline Lithium Salt: Efficient Synthesis of L-Proline and Isoindoloisoquinolinone Derivatives

被引:47
作者
Xu, Kun [1 ,2 ]
Zhang, Sheng [1 ,2 ]
Hu, Yanbin [1 ,2 ]
Zha, Zhenggen [1 ,2 ]
Wang, Zhiyong [1 ,2 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, CAS Key Lab Soft Matter Chem, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
asymmetric catalysis; enamines; lithium; Michael addition; proline; ENANTIOSELECTIVE CONJUGATE ADDITION; DIRECT ALDOL REACTION; AMINO-ACID; UNMODIFIED ALDEHYDES; ENAMINE CATALYSIS; KETONES; ORGANOCATALYSTS; COMPLEX; FUNCTIONALIZATION; MALONATE;
D O I
10.1002/chem.201202409
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Lithium makes it possible: The enantioselective Michael addition of aldehydes to nitroalkenes was catalyzed by the readily available proline lithium salt. Remarkably, the asymmetric Michael reaction was scaled up to 50 mmol with 23:1 d.r. and 90 % ee. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:3573 / 3578
页数:6
相关论文
共 118 条
  • [1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction
    Ahrendt, KA
    Borths, CJ
    MacMillan, DWC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) : 4243 - 4244
  • [2] Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene
    Alexakis, A
    Andrey, O
    [J]. ORGANIC LETTERS, 2002, 4 (21) : 3611 - 3614
  • [3] Organocatalytic asymmetric conjugate additions
    Almasi, Diana
    Alonso, Diego A.
    Najera, Carmen
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
  • [4] Origin and nature of lithium and hydrogen bonds to oxygen, sulfur, and selenium
    Ammal, SSC
    Venuvanalingam, P
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2000, 104 (46) : 10859 - 10867
  • [5] [Anonymous], 2010, Angew. Chem., DOI DOI 10.1002/ANGE.200905684
  • [6] [Anonymous], 2011, ANGEW CHEM
  • [7] [Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650
  • [8] Silyl-Modified Analogues of 2-Tritylpyrrolidine: Synthesis and Applications in Asymmetric Organocatalysis
    Bauer, Jonathan O.
    Stiller, Julian
    Marques-Lopez, Eugenia
    Strohfeldt, Katja
    Christmann, Mathias
    Strohmann, Carsten
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (42) : 12553 - 12558
  • [9] Enantioselective organocatalysis using SOMO activation
    Beeson, Teresa D.
    Mastracchio, Anthony
    Hong, Jun-Bae
    Ashton, Kate
    MacMillan, David W. C.
    [J]. SCIENCE, 2007, 316 (5824) : 582 - 585
  • [10] Berner OM, 2002, EUR J ORG CHEM, V2002, P1877