Super Bronsted acid catalysis

被引:130
作者
Cheon, Cheol Hong [1 ]
Yamamoto, Hisashi [1 ]
机构
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
关键词
DIELS-ALDER REACTION; SILICON LEWIS-ACIDS; SILYL ENOL ETHERS; MUKAIYAMA-ALDOL; PHOSPHORIC-ACID; ENANTIOSELECTIVE ALLYLBORATION; 1,3-DIPOLAR CYCLOADDITION; SUPERSUBSTITUENT =NSO2CF3; SQUARAMIDE DERIVATIVES; VERSATILE CATALYST;
D O I
10.1039/c0cc04867d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Bronsted acid catalysis has emerged as a new class of catalysis in modern organic synthesis. However, in order to make the utility of the Bronsted acid catalysis as broad as the well-developed Lewis acid catalysis, it is desirable to develop Bronsted acids demonstrating both high reactivities and selectivities. In this feature article, we will present our achievement in the design and development of strong Bronsted acids and their application to organic reactions. Furthermore, we will describe the Tf2NH-catalyzed Mukaiyama aldol reaction of super silyl enol ethers. We also will highlight the differences in reactivity and chemo- and stereo-selectivity between Bronsted and Lewis acid catalysis.
引用
收藏
页码:3043 / 3056
页数:14
相关论文
共 98 条
  • [21] Catalytic Asymmetric Transacetalization
    Coric, Ilija
    Vellalath, Sreekumar
    List, Benjamin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (25) : 8536 - +
  • [22] INORGANIC SOLID ACIDS AND THEIR USE IN ACID-CATALYZED HYDROCARBON REACTIONS
    CORMA, A
    [J]. CHEMICAL REVIEWS, 1995, 95 (03) : 559 - 614
  • [23] Curran DP, 2001, SYNLETT, P1488
  • [24] Denmark S.E., 2004, Modern Aldol Reactions, V2, P229
  • [25] Lewis base catalyzed enantioselective aldol addition of acetaldehyde-derived silyl enol ether to aldehydes
    Denmark, SE
    Bui, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) : 10190 - 10193
  • [26] Small-molecule H-bond donors in asymmetric catalysis
    Doyle, Abigail G.
    Jacobsen, Eric N.
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5713 - 5743
  • [27] Asymmetric Bronsted acid catalyzed isoindoline synthesis: Enhancement of enantiomeric ratio by stereoablative kinetic resolution
    Enders, Dieter
    Narine, Arun A.
    Toulgoat, Fabien
    Bisschops, Tom
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (30) : 5661 - 5665
  • [28] Enantioselective Organocatalytic Synthesis of Arylglycines via Friedel-Crafts Alkylation of Arenes with a Glyoxylate Imine
    Enders, Dieter
    Seppelt, Matthias
    Beck, Tobias
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (09) : 1413 - 1418
  • [29] A Powerful Chiral Counteranion Motif for Asymmetric Catalysis
    Garcia-Garcia, Pilar
    Lay, Frank
    Garcia-Garcia, Patricia
    Rabalakos, Constantinos
    List, Benjamin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (24) : 4363 - 4366
  • [30] Hydrogen bond catalyzed enantioselective vinylogous Mukaiyama aldol reaction
    Gondi, VB
    Gravel, M
    Rawal, VH
    [J]. ORGANIC LETTERS, 2005, 7 (25) : 5657 - 5660