Organocatalytic direct asymmetric α-heteroatom functionalization of aldehydes and ketones

被引:327
作者
Marigo, M [1 ]
Jorgensen, KA [1 ]
机构
[1] Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark
关键词
D O I
10.1039/b517090g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The direct enantioselective introduction of a stereogenic carbon-heteroatom bond adjacent to a carbonyl functionality leads to optically active compounds of significant importance for e.g. the life-science industry. Organocatalytic enantioselective amination, oxygenation, fluorination, chlorination, bromination and sulfenylation of aldehydes and ketones, using chiral amines as the catalysts, are reviewed in this feature article. Furthermore, a few other transformations are also outlined. The scope, potential and application of these organocatalytic asymmetric reactions are presented and the mechanistic aspects discussed.
引用
收藏
页码:2001 / 2011
页数:11
相关论文
共 74 条
[1]   Organocatalytic asymmetric hydroxylation of β-keto esters:: Metal-free synthesis of optically active anti-diols [J].
Acocella, MR ;
Mancheño, OG ;
Bella, M ;
Jorgensen, KA .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :8165-8167
[2]   Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions [J].
Allemann, C ;
Gordillo, R ;
Clemente, FR ;
Cheong, PHY ;
Houk, KN .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :558-569
[3]   Origins of opposite absolute stereloselectivities in proline-catalyzed direct Mannich and aldol reactions [J].
Bahmanyar, S ;
Houk, KN .
ORGANIC LETTERS, 2003, 5 (08) :1249-1251
[4]   Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity [J].
Bahmanyar, S ;
Houk, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11273-11283
[5]   Organocatalytic asymmetric α-halogenation of 1,3-dicarbonyl compounds [J].
Bartoli, G ;
Bosco, M ;
Carlone, A ;
Locatelli, M ;
Melchiorre, P ;
Sambri, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6219-6222
[6]   Enantioselective organocatalytic α-fluorination of aldehydes [J].
Beeson, TD ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (24) :8826-8828
[7]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[8]   Organocatalytic asymmetric α-bromination of aldehydes and ketones [J].
Bertelsen, S ;
Halland, N ;
Bachmann, S ;
Marigo, M ;
Braunton, A ;
Jorgensen, KA .
CHEMICAL COMMUNICATIONS, 2005, (38) :4821-4823
[9]   Direct catalytic enantioselective α-aminoxylation of ketones:: A stereoselective synthesis of α-hydroxy and α,α′-dihydroxy ketones [J].
Bogevig, A ;
Sundén, H ;
Córdova, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (09) :1109-1112
[10]  
Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO