New chiral synthon from the PLE catalyzed enantiomeric separation of 6-acetoxy-3-methylcyclohex-2-en-1-one

被引:26
作者
Tanyeli, C
Demir, AS
Dikici, E
机构
[1] Department of Chemistry, Middle East Technical University
关键词
D O I
10.1016/0957-4166(96)00296-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(+/-)-6-Acetoxy-3-methylcyclohex-2-en-1-one was resolved by PLE catalyzed hydrolysis to afford (+)-6-hydroxy-3-methylcyclohex-2-en-1-one in >95% e.e. (+)-6-Hydroxy-3-methylcyclohex-2-en-1-one was transformed to its (S)-O-acetyllactyl ester derivative to determine the e.e. %. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:2399 / 2402
页数:4
相关论文
共 9 条
[1]  
DEMIR AS, 1991, SYNTHESIS-STUTTGART, P719
[2]   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
[3]   SYNTHESIS OF QUASSINOIDS .3. OXIDATION OF ENONES TO ALPHA'-ACETOXYENONES USING MANGANESE TRIACETATE [J].
DUNLAP, NK ;
SABOL, MR ;
WATT, DS .
TETRAHEDRON LETTERS, 1984, 25 (51) :5839-5842
[4]   CLEAVAGE OF UNSATURATED ALPHA-KETOLS TO OMEGA-OXO-ALPHA,BETA-UNSATURATED ACIDS [J].
FLORESCA, R ;
KURIHARA, M ;
WATT, DS ;
DEMIR, A .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :2196-2200
[5]   STEREOISOMERIC FLAVOR COMPOUNDS .14. (S)-O-ACETYLLACTYL CHLORIDE - A VERSATILE CHIRAL AUXILIARY IN STEREODIFFERENTIATION OF ENANTIOMERIC FLAVOR COMPONENTS [J].
MOSANDL, A ;
GESSNER, M ;
GUNTHER, C ;
DEGER, W ;
SINGER, G .
JOURNAL OF HIGH RESOLUTION CHROMATOGRAPHY & CHROMATOGRAPHY COMMUNICATIONS, 1987, 10 (02) :67-70
[6]  
OPPOLZER W, 1975, TETRAHEDRON LETT, P3411
[7]  
Polonsky J, 1985, Fortschr Chem Org Naturst, V47, P221
[8]   ENZYMES IN ORGANIC-SYNTHESIS .47. ACTIVE-SITE MODEL FOR INTERPRETING AND PREDICTING THE SPECIFICITY OF PIG-LIVER ESTERASE [J].
TOONE, EJ ;
WERTH, MJ ;
JONES, JB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4946-4952
[9]  
WONG CH, 1995, ENZYMES SYNTHETIC OR, V12