Mechanistically Inspired Catalysts for Enantioselective Desymmetrizations by Olefin Metathesis

被引:38
作者
Fournier, Pierre-Andre [1 ]
Savoie, Jolaine [1 ]
Stenne, Brice [1 ]
Bedard, Marion [1 ]
Grandbois, Alain [1 ]
Collins, Shawn K. [1 ]
机构
[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
asymmetric catalysis; desymmetrization; N-heterocyclic carbenes; olefin metathesis; ruthenium;
D O I
10.1002/chem.200800642
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In asymmetric olefin metathesis reactions, the addition of halide additives is often required to augment enantioselectivities, despite the fact that the additives result in catalysts with diminished reactivities. The preparation of new chiral Ru-based catalysts was accomplished by exploiting previously reported mechanistic studies. The catalysts possess a high level of reactivity and successfully induce high levels of asymmetry in desymmetrization reactions without the use of halide additives.
引用
收藏
页码:8690 / 8695
页数:6
相关论文
共 40 条
[21]  
Hoveyda AH, 2001, CHEM-EUR J, V7, P945, DOI 10.1002/1521-3765(20010302)7:5<945::AID-CHEM945>3.0.CO
[22]  
2-3
[23]  
HOVEYDA AH, 2003, HDB METATHESIS, V2, pCH2
[24]   The remarkable metal-catalysed olefin metathesis reaction [J].
Hoveyda, Amir H. ;
Zhugralin, Adil R. .
NATURE, 2007, 450 (7167) :243-251
[25]   A sterically demanding nucleophilic carbene: 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene). Thermochemistry and catalytic application in olefin metathesis [J].
Jafarpour, L ;
Stevens, ED ;
Nolan, SP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 606 (01) :49-54
[26]   N,N'-dialkyl- and N-alkyl-N-mesityl-substituted N-heterocyclic carbenes as ligands in Grubbs catalysts [J].
Ledoux, Nele ;
Allaert, Bart ;
Pattyn, Siegfried ;
Vander Mierde, Hans ;
Vercaemst, Carl ;
Verpoort, Francis .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (17) :4654-4661
[27]   Nitro-substituted Hoveyda-Grubbs ruthenium carbenes: Enhancement of catalyst activity through electronic activation [J].
Michrowska, A ;
Bujok, R ;
Harutyunyan, S ;
Sashuk, V ;
Dolgonos, G ;
Grela, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9318-9325
[28]   A standard system of characterization for olefin metathesis catalysts [J].
Ritter, Tobias ;
Hejl, Andrew ;
Wenzel, Anna G. ;
Funk, Timothy W. ;
Grubbs, Robert H. .
ORGANOMETALLICS, 2006, 25 (24) :5740-5745
[29]  
Schrock R. R., 2003, ANGEW CHEM, V115, P4740, DOI DOI 10.1002/ANGE.200300576
[30]   Molybdenum and tungsten imido alkylidene complexes as efficient olefin-metathesis catalysts [J].
Schrock, RR ;
Hoveyda, AH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (38) :4592-4633