Radicals in asymmetric organocatalysis

被引:54
作者
Bertelsen, Soren [1 ]
Nielsen, Martin [1 ]
Jorgensen, Karl Anker [1 ]
机构
[1] Aarhus Univ, Dept Chem, Danish Natl Res Fdn Ctr Catalysis, DK-8000 Aarhus C, Denmark
关键词
asymmetric catalysis; carbonyl compounds; enamines; organocatalysis; radicals; RATE CONSTANTS; CHEMISTRY; CATALYSIS;
D O I
10.1002/anie.200702834
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Radical turn to organocatalysis: Amino-catalysis has developed into a versatile tool for the stereoselective functionalization of carbonyl species. In the search for new organocatalytic transformations, attention has been focused on radicals to expand the scope of aminocatalysis. The successful application of the SOMO(singly occupied molecular orbital)-enamine activation has led to a number of novel transformations. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7356 / 7359
页数:4
相关论文
共 46 条
[1]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[2]   Organocatalytic asymmetric conjugate additions [J].
Almasi, Diana ;
Alonso, Diego A. ;
Najera, Carmen .
TETRAHEDRON-ASYMMETRY, 2007, 18 (03) :299-365
[3]  
[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[4]   Catalytic enantioselective reactions driven by photoinduced electron transfer [J].
Bauer, A ;
Westkämper, F ;
Grimme, S ;
Bach, T .
NATURE, 2005, 436 (7054) :1139-1140
[5]   Enantioselective organocatalysis using SOMO activation [J].
Beeson, Teresa D. ;
Mastracchio, Anthony ;
Hong, Jun-Bae ;
Ashton, Kate ;
MacMillan, David W. C. .
SCIENCE, 2007, 316 (5824) :582-585
[6]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[7]   Dienamine catalysis:: Organocatalytic asymmetric γ-amination of α,β unsaturated aldehydes [J].
Bertelsen, Slren ;
Marigo, Mauro ;
Brandes, Sebastian ;
Diner, Peter ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12973-12980
[8]   AN EFFICIENT SYNTHESIS OF 1,2,9,9A-TETRAHYDROCYCLOPROPA[C]BENZ[E]INDOL-4-ONE (CBI) - AN ENHANCED AND SIMPLIFIED ANALOG OF THE CC-1065 AND DUOCARMYCIN ALKYLATION SUBUNITS [J].
BOGER, DL ;
MCKIE, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1271-1275
[9]   The direct and enantioselective organocatalytic α-oxidation of aldehydes [J].
Brown, SP ;
Brochu, MP ;
Sinz, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10808-10809
[10]   Carbohydrate-derived thiols as protic polarity-reversal catalysts for enantioselective radical-chain reactions [J].
Cai, YD ;
Roberts, BP ;
Tocher, DA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (11) :1376-1386