Developments in Chiral Binaphthyl-Derived Bronsted/Lewis Acids and Hydrogen-Bond-Donor Organocatalysis

被引:159
作者
Schenker, Sebastian [1 ]
Zamfir, Alexandru [1 ]
Freund, Matthias [1 ]
Tsogoeva, Svetlana B. [1 ]
机构
[1] Univ Erlangen Nurnberg, Dept Chem & Pharm, Chair Organ Chem 1, D-91054 Erlangen, Germany
关键词
Organocatalysis; Bronsted acids; Lewis acids; Hydrogen bonds; Binaphthyl derivatives; BAYLIS-HILLMAN REACTION; LEWIS-BASE ACTIVATION; SILYL KETENE ACETALS; N-BOC IMINES; DICARBOXYLIC-ACID; ENANTIOSELECTIVE ADDITION; ASYMMETRIC ALLYLBORATION; CATALYSIS; MECHANISM; DESIGN;
D O I
10.1002/ejoc.201001538
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In recent years, binaphthyl compounds have found frequent applications in the design of various asymmetric organocatalysts, because binaphthyl structures are an attractive platform for organocatalyst development, particularly in light of their axial chirality characteristic. In this review, we discuss recent achievements in developing enantioselective transformations by using catalysts derived from axially chiral binaphthyls: Bronsted acids (different from BINOL-phosphates), Lewis acids, and hydrogen-bond donors. Results published after 2004 through 2010 are presented.
引用
收藏
页码:2209 / 2222
页数:14
相关论文
共 83 条
[1]   Stronger bronsted acids [J].
Akiyama, Takahiko .
CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758
[2]   Recent progress in chiral Bronsted acid catalysis [J].
Akiyama, Takahiko ;
Itoh, Junji ;
Fuchibe, Kohei .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) :999-1010
[3]  
[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[4]  
ARMAREGO WMF, 2003, PURIFICATION LAB CHE, P132
[5]  
Barnett D. S., 2009, ANGEW CHEM, V121, P8835
[6]   The Mechanism and an Improved Asymmetric Allylboration of Ketones Catalyzed by Chiral Biphenols [J].
Barnett, David S. ;
Moquist, Philip N. ;
Schaus, Scott E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (46) :8679-8682
[7]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[8]  
Bishop J. A., 2009, ANGEW CHEM, V121, P4401
[9]   Enantioselective Addition of Boronates to Acyl Imines Catalyzed by Chiral Biphenols [J].
Bishop, Joshua A. ;
Lou, Sha ;
Schaus, Scott E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (24) :4337-4340
[10]   A Bronsted acid catalyst for the enantioselective protonation reaction [J].
Cheon, Cheol Hong ;
Yamamoto, Hisashi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9246-+