Laccase/TEMPO-mediated system for the thermodynamically disfavored oxidation of 2,2-dihalo-1-phenylethanol derivatives

被引:46
作者
Alba Diaz-Rodriguez, Kinga Kedziora [1 ]
Lavandera, Ivan [1 ]
Gotor-Fernandez, Vicente [1 ]
Gotor, Vicente [1 ]
机构
[1] Univ Oviedo, Inst Univ Biotecnol Asturias, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain
关键词
DYNAMIC KINETIC RESOLUTION; LIGNIN MODEL; CATALYZED OXIDATION; SECONDARY ALCOHOLS; ORGANIC-SYNTHESIS; EFFICIENT ROUTE; ENZYME LACCASE; TEMPO; RACEMIZATION; KETONES;
D O I
10.1039/c4gc00066h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient methodology to oxidize beta,beta-dihalogenated secondary alcohols employing oxygen was achieved in a biphasic medium using the laccase from Trametes versicolor/TEMPO pair, providing the corresponding ketones in a clean fashion under very mild conditions. Moreover, a chemoenzymatic protocol has been applied successfully to deracemize 2,2-dichloro-1-phenylethanol combining this oxidation with an alcohol dehydrogenase-catalyzed bioreduction.
引用
收藏
页码:2448 / 2453
页数:6
相关论文
共 75 条
[1]   Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation [J].
Alfonsi, Kim ;
Colberg, Juan ;
Dunn, Peter J. ;
Fevig, Thomas ;
Jennings, Sandra ;
Johnson, Timothy A. ;
Kleine, H. Peter ;
Knight, Craig ;
Nagy, Mark A. ;
Perry, David A. ;
Stefaniak, Mark .
GREEN CHEMISTRY, 2008, 10 (01) :31-36
[2]   OXIDATION OF DIOLS WITH ALKALI HYPOCHLORITES CATALYZED BY OXAMMONIUM SALTS UNDER 2-PHASE CONDITIONS [J].
ANELLI, PL ;
BANFI, S ;
MONTANARI, F ;
QUICI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2970-2972
[3]  
Ardens I. W. C. E., 2006, BIOCATAL BIOTRANSFOR, V24, P443
[4]  
Arends I.W. C. E., 2010, Modern Oxidation Methods, P147, DOI DOI 10.1002/9783527632039.CH5
[5]   Comparison of TEMPO and its derivatives as mediators in laccase catalysed oxidation of alcohols [J].
Arends, Isabel W. C. E. ;
Li, Yu-Xin ;
Ausan, Rina ;
Sheldon, Roger A. .
TETRAHEDRON, 2006, 62 (28) :6659-6665
[6]   One pot three-component regioselective and diastereoselective synthesis of halogenated pyrido[2,1-b][1,3]oxazines [J].
Asghari, Sakineh ;
Habibi, Ahmad Khabbazi .
TETRAHEDRON, 2012, 68 (43) :8890-8898
[7]   The mechanism of the haloform reaction - The preparation of mixed haloforms [J].
Aston, JG ;
Newkirk, JD ;
Dorsky, J ;
Jenkins, DM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :1413-1416
[8]   The course of reaction in the transformation of alpha,alpha-dibromoacetophenone to mandelic acid by means of aqueous alkali [J].
Ayres, EB ;
Hauser, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1943, 65 :1095-1096
[9]   Towards environmentally benign catalytic oxidation [J].
Baiker, Alfons ;
Mallat, Tamas .
CATALYSIS SCIENCE & TECHNOLOGY, 2013, 3 (02) :267-267
[10]   Laccase/mediated oxidation of a lignin model for improved delignification procedures [J].
Barreca, AM ;
Fabbrini, M ;
Galli, C ;
Gentili, P ;
Ljunggren, S .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2003, 26 (1-2) :105-110