BIOCATALYTIC RESOLUTION OF 2,3-EPOXYALCOHOLS IN ORGANIC-SOLVENTS

被引:14
作者
KANERVA, LT
VANTTINEN, E
机构
[1] Department of Chemistry, University of Turku
关键词
D O I
10.1016/S0957-4166(00)86018-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The PPL-catalysed resolution of 3-substituted cis-2,3-epoxyalcohols has been successfully performed in toluene and in THF. Lower enantioselectivities were observed for the trans-isomers. A substituent at the position 3 of an epoxyalcohol controls the enantiomeric discrimination, the 3R centre always occuring in the enantiomer which reacts faster.
引用
收藏
页码:85 / 90
页数:6
相关论文
共 28 条
[11]   ALLYLIC CHLORIDES .12. PREPARATION AND PROPERTIES OF CISCINNAMYL AND TRANS-CINNAMYL CHLORIDE [J].
HATCH, LF ;
ALEXANDER, HE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (12) :5643-5645
[12]   ENZYMES IN ORGANIC-SYNTHESIS .48. PIG-LIVER ESTERASE AND PORCINE PANCREATIC LIPASE CATALYZED HYDROLYSES OF 3,4-(ISOPROPYLIDENEDIOXY)-2,5-TETRAHYDROFURANYL DIESTERS [J].
HULTIN, PG ;
MUESELER, FJ ;
JONES, JB .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5375-5380
[13]   DILEMMA REGARDING AN ACTIVE-SITE MODEL FOR PORCINE PANCREATIC LIPASE [J].
HULTIN, PG ;
JONES, JB .
TETRAHEDRON LETTERS, 1992, 33 (11) :1399-1402
[14]   SOLVENT EFFECTS IN LIPASE-CATALYZED TRANSESTERIFICATION REACTIONS [J].
KANERVA, LT ;
VIHANTO, J ;
HALME, MH ;
LOPONEN, JM ;
EURANTO, EK .
ACTA CHEMICA SCANDINAVICA, 1990, 44 (10) :1032-1035
[15]   HAMMETT ANALYSIS OF ENZYME ACTION IN ORGANIC-SOLVENTS [J].
KANERVA, LT ;
KLIBANOV, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6864-6865
[16]  
KATSUKI T, 1980, J AM CHEM SOC, V102, P5976
[17]   RESOLUTION OF RACEMIC MIXTURES VIA LIPASE CATALYSIS IN ORGANIC-SOLVENTS [J].
KIRCHNER, G ;
SCOLLAR, MP ;
KLIBANOV, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7072-7076
[18]   ASYMMETRIC TRANSFORMATIONS CATALYZED BY ENZYMES IN ORGANIC-SOLVENTS [J].
KLIBANOV, AM .
ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (04) :114-120
[19]   ENZYMATIC CATALYSIS IN ANHYDROUS ORGANIC-SOLVENTS [J].
KLIBANOV, AM .
TRENDS IN BIOCHEMICAL SCIENCES, 1989, 14 (04) :141-144
[20]   LIPASE-CATALYZED HYDROLYSIS AS A ROUTE TO ESTERS OF CHIRAL EPOXY ALCOHOLS [J].
LADNER, WE ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (23) :7250-7251