4.15 C–C Bond Formation

作者: H. Miyabe , T. Naito

DOI: 10.1016/B978-0-08-095167-6.00414-6

关键词: CatalysisRadicalLewis acids and basesBond formationOrganic chemistryChemistryOrganic synthesisEnantioselective synthesis

摘要: Radical chemistry is amenable to ‘green’ based on the performance in water and with a variety of cheap, environmentally benign reagents. has developed into one most powerful tools for carboncarbon bond formation organic synthesis. Enantioselective radical reactions have been intensively studied over past 10 years and, although many important advances made by using chiral Lewis acids, it far from mature area particularly, enantioselective approaches via catalysts remain largely elusive. However, very recent works organocatalytic reaction undoubtedly show new avenue that will be pursued coming years. The chapter concentrates route involving catalytic covering literatures available 2001 through 2010. Research continues blossom future well assured.

参考文章(74)
Sunggi Lee, Chae Jo Lim, Sunggak Kim, Rajesh Subramaniam, Jake Zimmerman, Mukund P. Sibi, Enantioselective conjugate radical addition to alpha'-hydroxy enones. Organic Letters. ,vol. 8, pp. 4311- 4313 ,(2006) , 10.1021/OL061634Z
Olivier Corminboeuf, Philippe Renaud, N-alkoxyacrylamides as substrates for enantioselective Diels-Alder reactions. Organic Letters. ,vol. 4, pp. 1735- 1738 ,(2002) , 10.1021/OL0257981
Philip Garner, James T. Anderson, Philip B. Cox, Stephen J. Klippenstein, Ray Leslie, Noemi Scardovi, Development of an effective chiral auxiliary for hydroxyalkyl radicals. Journal of Organic Chemistry. ,vol. 67, pp. 6195- 6209 ,(2002) , 10.1021/JO010880F
Dan Yang, Qiang Gao, Bao-Fu Zheng, Nian-Yong Zhu, Et2AlCl-Promoted Asymmetric Phenylseleno Group Transfer Radical Cyclization Reactions of Unsaturated β-Hydroxy Esters Journal of Organic Chemistry. ,vol. 69, pp. 8821- 8828 ,(2004) , 10.1021/JO048322Z
Sunggi Lee, Sunggak Kim, Enantioselective Radical Conjugate Addition to α′-Phosphoric Enones† Organic Letters. ,vol. 10, pp. 4255- 4258 ,(2008) , 10.1021/OL8017177
David A. Nagib, Mark E. Scott, David W. C. MacMillan, Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis Journal of the American Chemical Society. ,vol. 131, pp. 10875- 10877 ,(2009) , 10.1021/JA9053338
Zhibin Luo, Quanzhong Liu, Liuzhu Gong, Xin Cui, Aiqiao Mi, Yaozhong Jiang, The rational design of novel chiral oxovanadium(IV) complexes for highly enantioselective oxidative coupling of 2-naphthols. Chemical Communications. pp. 914- 915 ,(2002) , 10.1039/B201351G
Carol A. Mulrooney, Xiaolin Li, Evan S. DiVirgilio, Marisa C. Kozlowski, General approach for the synthesis of chiral perylenequinones via catalytic enantioselective oxidative biaryl coupling. Journal of the American Chemical Society. ,vol. 125, pp. 6856- 6857 ,(2003) , 10.1021/JA027745K
W. Grimme, H. Hoffmann, E. Vogel, Synthesis of the Bicyclo[5,4,1]dodecapentaenylium Cation – a Carbonium Ion with 10 π-Electrons Angewandte Chemie. ,vol. 4, pp. 354- 355 ,(1965) , 10.1002/ANIE.196503542