Simple chemoenzymatic access to enantiopure pharmacologically interesting (R)-2-hydroxypropiophenones

被引:34
作者
Demir, AS [1 ]
Hamamci, H
Sesenoglu, O
Aydogan, F
Capanoglu, D
Neslihanoglu, R
机构
[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey
[2] Middle E Tech Univ, Dept Biotechnol, TR-06531 Ankara, Turkey
[3] Middle E Tech Univ, Dept Food Engn, TR-06531 Ankara, Turkey
关键词
D O I
10.1016/S0957-4166(01)00346-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A chemoenzymatic synthesis of pharmacological interesting (R)-2-hydroxypropiophenones starting from propiophenone derivatives is described. Manganese(III) acetate-mediated acetoxylation followed by fungus-mediated hydrolysis of propiophenone derivatives affords (R)-2-hydroxypropiophenones in high enantiomeric excess. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1953 / 1956
页数:4
相关论文
共 31 条
[1]   Biocatalytic synthesis of optically active α-oxyfunctionalized carbonyl compounds [J].
Adam, W ;
Lazarus, M ;
Saha-Möller, CR ;
Schreier, P .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (10) :837-845
[2]   Synthesis, stereochemistry and anti-tetrabenazine activity of bicyclo analogues of 2-phenylmorpholines [J].
Boswell, GE ;
Musso, DL ;
Davis, AO ;
Kelley, JL ;
Soroko, FE ;
Cooper, BR .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (06) :1813-1820
[3]  
Coppola G.M., 1997, BETA HYDROXY ACIDS E
[4]   ASYMMETRIC HYDROXYLATION OF ENOLATES WITH N-SULFONYLOXAZIRIDINES [J].
DAVIS, FA ;
CHEN, BC .
CHEMICAL REVIEWS, 1992, 92 (05) :919-934
[5]   Asymmetric benzoin reaction catalyzed by benzoylformate decarboxylase [J].
Demir, AS ;
Dünnwald, T ;
Iding, H ;
Pohl, M ;
Müller, M .
TETRAHEDRON-ASYMMETRY, 1999, 10 (24) :4769-4774
[6]   Enantioselective synthesis of hydroxy ketones through cleavage and formation of acyloin linkage.: Enzymatic kinetic resolution via C-C bond cleavage [J].
Demir, AS ;
Pohl, M ;
Janzen, E ;
Müller, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (07) :633-635
[7]   Synthesis and Rhizopus oryzae mediated enantioselective hydrolysis of α-acetoxy aryl alkyl ketones [J].
Demir, AS ;
Hamamci, H ;
Tanyeli, C ;
Akhmedov, IM ;
Doganel, F .
TETRAHEDRON-ASYMMETRY, 1998, 9 (10) :1673-1677
[8]  
DEMIR AS, 1992, SYNTHESIS-STUTTGART, P235
[9]   Butenolide annelation using a manganese(III) oxidation.: A synthesis of 4-arylfuran-2(5H)-ones [J].
Demir, AS ;
Camkerten, N ;
Gercek, Z ;
Duygu, N ;
Reis, O ;
Arikan, E .
TETRAHEDRON, 1999, 55 (08) :2441-2448
[10]   OXIDATION OF ARYL ALKYL KETONES TO ALPHA-ACYLOXY, ALPHA-(CAMPHORSULFONYLOXY), OR ALPHA-HYDROXY DERIVATIVES USING MANGANESE(III) ACETATE IN COMBINATION WITH CARBOXYLIC-ACIDS OR (1S)-(+)-10-CAMPHORSULFONIC ACID [J].
DEMIR, AS ;
CAMKERTEN, N ;
AKGUN, H ;
TANYELI, C ;
MAHASNEH, AS ;
WATT, DS .
SYNTHETIC COMMUNICATIONS, 1990, 20 (15) :2279-2289