Enantioselective Catalysis of Photochemical Reactions

被引:523
作者
Brimioulle, Richard [1 ,2 ]
Lenhart, Dominik [1 ,2 ]
Maturi, Mark M. [1 ,2 ]
Bach, Thorsten [1 ,2 ]
机构
[1] Tech Univ Munich, Lehrstuhl Organ Chem 1, D-85747 Garching, Germany
[2] Tech Univ Munich, CRC, D-85747 Garching, Germany
关键词
asymmetric catalysis; enantioselectivity; homogeneous catalysis; photocatalysis; photochemistry; LEWIS-ACID CATALYSIS; INTRAMOLECULAR 2+2 PHOTOCYCLOADDITION; Z-E PHOTOISOMERIZATION; DIELS-ALDER REACTION; ENANTIODIFFERENTIATING POLAR ADDITION; CONTROLLED SUPRAMOLECULAR PHOTOCHIROGENESIS; ANTI-MARKOVNIKOV PHOTOADDITION; MERGING PHOTOREDOX CATALYSIS; CIS-TRANS-PHOTOISOMERIZATION; NORRISH-YANG CYCLIZATION;
D O I
10.1002/anie.201411409
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The nature of the excited state renders the development of chiral catalysts for enantioselective photochemical reactions a considerable challenge. The absorption of a 400 nm photon corresponds to an energy uptake of approximately 300 kJ mol(-1). Given the large distance to the ground state, innovative concepts are required to open reaction pathways that selectively lead to a single enantiomer of the desired product. This Review outlines the two major concepts of homogenously catalyzed enantioselective processes. The first part deals with chiral photocatalysts, which intervene in the photochemical key step and induce an asymmetric induction in this step. In the second part, reactions are presented in which the photochemical excitation is mediated by an achiral photocatalyst and the transfer of chirality is ensured by a second chiral catalyst (dual catalysis).
引用
收藏
页码:3872 / 3890
页数:19
相关论文
共 225 条
[71]  
Gao YY, 2004, J INCL PHENOM MACRO, V50, P111, DOI 10.1007/s10847-004-8850-8
[72]   Lewis-acid-catalyzed photodimerization of coumarins and N-methyl-2-quinolone [J].
Goerner, Helmut ;
Wolff, Thomas .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 2008, 84 (05) :1224-1230
[73]   Highly enantioselective Diels-Alder reaction of a photochemically generated o-quinodimethane with olefins [J].
Grosch, B ;
Orlebar, CN ;
Herdtweck, E ;
Massa, W ;
Bach, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3693-3696
[74]   1-METHOXYCARBONYL-SUBSTITUTED 2,3-DIHYDROPYRIDIN-4(1H)-ONE (METHYL 1,2,3,4-TETRAHYDRO-4-OXOPYRIDINE-1-CARBOXYLATE) AS CHROMOPHORE FOR PHOTOCHEMICAL [2+2]-CYCLOADDITIONS [J].
GUERRY, P ;
BLANCO, P ;
BRODBECK, H ;
PASTERIS, O ;
NEIER, R .
HELVETICA CHIMICA ACTA, 1991, 74 (01) :163-178
[75]   THE PHOTOCHEMICAL[2+2]CYCLOADDITION TO N-METHOXYCARBONYL-5,6-DIHYDRO-4-PYRIDONE [J].
GUERRY, P ;
NEIER, R .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (22) :1727-1728
[76]  
GUERRY P, 1987, CHIMIA, V41, P341
[77]  
Guo H., 2010, ANGEW CHEM, V122, P7948
[78]   Enantioselective Lewis Acid Catalysis in Intramolecular [2+2] Photocycloaddition Reactions of Coumarins [J].
Guo, Hao ;
Herdtweck, Eberhardt ;
Bach, Thorsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (42) :7782-7785
[79]   Cobalt(I)-catalyzed asymmetric [2+2+2] cycloaddition of alkynes and nitriles: Synthesis of enantiomerically enriched atropoisomers of 2-arylpyridines [J].
Gutnov, A ;
Heller, B ;
Fischer, C ;
Drexler, HJ ;
Spannenberg, A ;
Sundermann, B ;
Sundermann, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3795-3797
[80]  
Gutnov A., 2004, ANGEW CHEM, V116, P3883