Super Bronsted acid catalysis

被引:133
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
[72]   Synthesis of BINOL derived phosphorodithioic acids as new chiral Bronsted acids and an improved synthesis of 3,3′-disubstituted H8-BINOL derivatives [J].
Pousse, Guillaume ;
Devineau, Alice ;
Dalla, Vincent ;
Humphreys, Luke ;
Lasne, Marie-Claire ;
Rouden, Jacques ;
Blanchet, Jerome .
TETRAHEDRON, 2009, 65 (51) :10617-10622
[73]   Catalytic enantioselective and catalyst-controlled diastereofacial-selective additions of allyl- and crotylboronates to aldehydes using chiral bronsted acids [J].
Rauniyar, V ;
Hall, DG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (15) :2426-2428
[74]   Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol•SnCl4 complexes.: Optimization, substrate scope and mechanistic investigations [J].
Rauniyar, Vivek ;
Zhai, Huimin ;
Hall, Dennis G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (26) :8481-8490
[75]   Rationally Improved Chiral Bronsted Acid for Catalytic Enantioselective Allylboration of Aldehydes with an Expanded Reagent Scope [J].
Rauniyar, Vivek ;
Hall, Dennis G. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11) :4236-4241
[76]   Enantioselective aza-Henry reaction with an N-sulfinyl urea organocatalyst [J].
Robak, MaryAnn T. ;
Trincado, Monica ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) :15110-+
[77]   Bronsted acid-catalyzed desymmetrization of meso-aziridines [J].
Rowland, Emily B. ;
Rowland, Gerald B. ;
Rivera-Otero, Edwin ;
Antilla, Jon C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (40) :12084-+
[78]   Asymmetric bronsted acid catalysis: Enantioselective nucleophilic substitutions and 1,4-additions [J].
Rueping, Magnus ;
Nachtsheim, Boris J. ;
Moreth, Stefan A. ;
Bolte, Michael .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (03) :593-596
[79]   Chiral Bronsted acids in the catalytic asymmetric Nazarov cyclization - The first enantioselective organocatalytic electrocyclic reaction [J].
Rueping, Magnus ;
Ieawsuwan, Winai ;
Antonchick, Andrey P. ;
Nachtsheim, Boris J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (12) :2097-2100
[80]   A Catalytic Asymmetric Electrocyclization-Protonation Reaction [J].
Rueping, Magnus ;
Ieawsuwan, Winai .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (1-2) :78-84