Enzymatic resolution of (RS)-p-hydroxy selenides in organic media

被引:23
作者
Costa, CE
Clososki, GC
Barchesi, HB
Zanotto, SP
Nascimento, MG
Comasseto, JV
机构
[1] Univ Sao Paulo, Inst Quim, BR-05599070 Sao Paulo, SP, Brazil
[2] Univ Fed Santa Catarina, Dept Quim, BR-88040900 Florianopolis, SC, Brazil
关键词
D O I
10.1016/j.tetasy.2004.11.007
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Kinetic resolutions of a number of beta-hydroxy selenides promoted by enzymes were performed using PPL (free Porcine pancreatic lipase), PSL (Amano PS-free Pseudomonas sp. lipase) and CALB (NOVOZYM 435(R)-immobilized Candida Antarctica lipase type B) with (RS)-1-phenylselanyl-propan-2-ol. CALB gave the best results and provided both (R)- and (S)-enantiomers in high enantiomeric purity. A comparative study of the effect of temperature, solvent, enzyme immobilization and the structure of the substrates on the resolution is presented. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3945 / 3954
页数:10
相关论文
共 21 条
[1]   Asymmetric synthesis of arylselenoalcohols by means of the reduction of organoseleno acetophenones by whole fungal cells [J].
Andrade, LH ;
Omori, AT ;
Porto, ALM ;
Comasseto, JV .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2004, 29 (1-6) :47-54
[2]  
Back T. G., 1999, ORGANOSELENIUM CHEM
[3]   Diastereocontrol by a hydroxyl auxiliary in the synthesis of pyrrolidines via radical cyclization [J].
Besev, M ;
Engman, L .
ORGANIC LETTERS, 2002, 4 (18) :3023-3025
[4]   SYNTHESIS OF SELENOACETALS [J].
CLAREMBEAU, M ;
CRAVADOR, A ;
DUMONT, W ;
HEVESI, L ;
KRIEF, A ;
LUCCHETTI, J ;
VANENDE, D .
TETRAHEDRON, 1985, 41 (21) :4793-4812
[5]   Deracernization of aryl ethanols and reduction of acetophenones by whole fungal cells of Aspergillus terreus CCT 4083, A-terreus CCT 3320 and Rhizopus oryzae CCT 4964 [J].
Comasseto, JV ;
Andrade, LH ;
Omori, AT ;
Assis, LF ;
Porto, ALM .
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2004, 29 (1-6) :55-61
[6]   Preparation of chiral organochalcogeno-α-methylbenzyl alcohols via biocatalysis.: The role of Daucus carota root [J].
Comasseto, JV ;
Omori, AT ;
Porto, ALM ;
Andrade, LH .
TETRAHEDRON LETTERS, 2004, 45 (03) :473-476
[7]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[8]   Biocatalysis and enzymes in organic synthesis [J].
Davis, BG ;
Borer, V .
NATURAL PRODUCT REPORTS, 2001, 18 (06) :618-640
[9]  
Faber K., 2000, BIOTRANSFORMATION OR
[10]  
FERRABOSCHI P, 1990, SYNLETT, P545