Chiral phosphine oxides in present-day organocatalysis

被引:135
作者
Benaglia, Maurizio [1 ]
Rossi, Sergio [1 ]
机构
[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
关键词
CATALYTIC ENANTIOSELECTIVE CYANOSILYLATION; LEWIS-BASE ACTIVATION; ASYMMETRIC ALLYLATION; ALDOL REACTION; ALDEHYDES; KETONES; BINAPO; ACIDS;
D O I
10.1039/c004681g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The design and synthesis of new chiral Lewis bases is a field of extraordinary activity; in this context, while N-oxides derived from both N-heterocyclic systems and aliphatic amines have found widespread applications in organocatalysis, quite surprisingly phosphine oxides have been used less frequently. This contribution will highlight the relatively few examples of stereoselective transformations organocatalyzed by chiral phosphine oxides, discussing the different proposed reaction mechanisms and identifying topics for future investigation in what can be most certainly defined as an "Emerging Area".
引用
收藏
页码:3824 / 3830
页数:7
相关论文
共 41 条
[1]   Stereoselective reactions involving hypervalent silicate complexes [J].
Benaglia, Maurizio ;
Guizzetti, Stefania ;
Pignataro, Luca .
COORDINATION CHEMISTRY REVIEWS, 2008, 252 (5-7) :492-512
[2]   Organocatalysis mediated by (thio)urea derivatives [J].
Connon, Stephen J. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) :5418-5427
[3]   Enantioselective [3+2]-cycloadditions catalyzed by a protected, multifunctional phosphine-containing α-amino acid [J].
Cowen, Bryan J. ;
Miller, Scott J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (36) :10988-+
[4]   Enantioselective catalysis and complexity generation from allenoates [J].
Cowen, Bryan J. ;
Miller, Scott J. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3102-3116
[5]   Lewis base catalysis in organic synthesis [J].
Denmark, Scott E. ;
Beutner, Gregory L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (09) :1560-1638
[6]   Lewis base activation of Lewis acids: Catalytic enantioselective glycolate aldol reactions [J].
Denmark, Scott E. ;
Chung, Won-Jin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1890-1892
[7]   Neutral and cationic phosphoramide adducts of silicon tetrachloride: Synthesis and characterization of their solution and solid-state structures [J].
Denmark, Scott E. ;
Eklov, Brian M. .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (01) :234-239
[8]   Chiral phosphoramide-catalyzed enantioselective addition of allylic trichlorosilanes to aldehydes. Preparative and mechanistic studies with monodentate phosphorus-based amides [J].
Denmark, SE ;
Fu, JP ;
Coe, DM ;
Su, XP ;
Pratt, NE ;
Griedel, BD .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04) :1513-1522
[9]   Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones [J].
Denmark, SE ;
Fu, JP .
CHEMICAL REVIEWS, 2003, 103 (08) :2763-2793
[10]   Lewis base activation of Lewis acids. Addition of silyl ketene acetals to aldehydes [J].
Denmark, SE ;
Wynn, T ;
Beutner, GL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) :13405-13407