Lewis Base Assisted Bronsted Base Catalysis: Bidentate Phosphine Oxides as Activators and Modulators of Bronsted Basic Lanthanum-Aryloxides

被引:46
|
作者
Morimoto, Hiroyuki [1 ]
Yoshino, Tatsuhiko [1 ]
Yukawa, Takafumi [1 ]
Lu, Gang [1 ]
Matsunaga, Shigeki [1 ]
Shibasaki, Masakatsu [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
amino acids; Bronsted bases; combined catalysis; lanthanum; Lewis bases;
D O I
10.1002/anie.200803682
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Dynamic Duo: A Lewis basic bidentate phosphine oxide was effective for activating and modulating the properties of Brønsted basic lanthanum aryl oxides. The Lewis base 1/lanthanum aryl oxide system was suitable for anti-selective Mannich-type reactions of trichloromethyl ketones (see scheme), affording unique building blocks for azetidine-2-carboxylic acids as well as β-amino acids. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:9125 / 9129
页数:5
相关论文
共 25 条
  • [1] Lewis Base Assisted Bronsted Base Catalysis: Direct Asymmetric Allylic Alkylation of Indenes
    Cui, Hai-Lei
    Sun, Xun-Hao
    Jiang, Lin
    Dong, Lin
    Chen, Ying-Chun
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (36) : 7366 - 7371
  • [2] Lewis Base Assisted Bronsted Base Catalysis: Direct Regioselective Asymmetric Vinylogous Alkylation of Allylic Sulfones
    Jiang, Lin
    Lei, Qian
    Huang, Xin
    Cui, Hai-Lei
    Zhou, Xue
    Chen, Ying-Chun
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (34) : 9489 - 9493
  • [3] Enantioselective Bromocycloetherification by Lewis Base/Chiral Bronsted Acid Cooperative Catalysis
    Denmark, Scott E.
    Burk, Matthew T.
    ORGANIC LETTERS, 2012, 14 (01) : 256 - 259
  • [4] "Goldilocks Effect" of Water in Lewis-Bronsted Acid and Base Catalysis
    Barron, Benedict J.
    Wong, Wing-Tak
    Chiu, Pauline
    Hii, King Kuok
    ACS CATALYSIS, 2016, 6 (07): : 4189 - 4194
  • [5] Lewis Base Assisted Lithium Bronsted Base Catalysis: A New Entry for Catalytic Asymmetric Synthesis of β2,2-Amino Acids
    Amemiya, Fuyuki
    Noda, Hidetoshi
    Shibasaki, Masakatsu
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2019, 67 (10) : 1046 - 1049
  • [6] Designing the adequate base solid catalyst with Lewis or Bronsted basic sites or with acid-base pairs
    Climent, MJ
    Corma, A
    Iborra, S
    Velty, A
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 182 (01) : 327 - 342
  • [7] Bronsted Base/Lewis Acid Cooperative Catalysis in the Enantioselective Conia-Ene Reaction
    Yang, Ting
    Ferrali, Alessandro
    Sladojevich, Filippo
    Campbell, Leonie
    Dixon, Darren J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (26) : 9140 - +
  • [8] Direct Catalytic Asymmetric Addition of Allyl Cyanide to Ketones via Soft Lewis Acid/Hard Bronsted Base/Hard Lewis Base Catalysis
    Yazaki, Ryo
    Kumagai, Naoya
    Shibasaki, Masakatsu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) : 5522 - 5531
  • [9] Application of Chiral Lewis Base/Bronsted Acid Synergistic Catalysis Strategy in Enantioselective Synthesis of Organic Sulfides
    Zhu Deng
    Chen Zhi-Min
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (10) : 3015 - 3032
  • [10] Development and Mechanism of an Enantioselective Bromocycloetherification Reaction via Lewis Base/Chiral BrOnsted Acid Cooperative Catalysis
    Denmark, Scott E.
    Burk, Matthew T.
    CHIRALITY, 2014, 26 (07) : 344 - 355