Lipase-catalyzed enantioselective synthesis of methyl (R)- and (S)-2-tetradecyloxiranecarboxylate through sequential kinetic resolution

被引:22
作者
Jimenez, O [1 ]
Bosch, MP [1 ]
Guerrero, A [1 ]
机构
[1] CSIC,CID,DEPT BIOL ORGAN CHEM,ES-08034 BARCELONA,SPAIN
关键词
D O I
10.1021/jo970109y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Among a variety of lipases tested, Pseudomonas fluorescens lipase has been found to induce enantioselective acylation of methyl (R,S)-2-hydroxy-2-(hydroxymethyl)hexadecanoate (3), affording, through sequential kinetic resolution, both enantiomers in good optical yields. Efficiency of the process has been compared to the Sharpless asymmetric dihydroxylation of alkene 2 using (DHQD)(2)PHAL and (DHQ)(2)PHAL as chiral ligands. The (R)- and (S)-3 enantiomers have been cyclized to afford both enantiomers of methyl 2-tetradecyloxiranecarboxylate (1), a potent hypoglycemic agent and inhibitor of long-chain fatty acid oxidation.
引用
收藏
页码:3496 / 3499
页数:4
相关论文
共 29 条
[1]   MAJOR IMPROVEMENT IN OSMIUM CATALYZED VICINAL HYDROXYLATION OF OLEFINS BY TERT-BUTYL HYDROPEROXIDE [J].
AKASHI, K ;
PALERMO, RE ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :2063-2066
[2]   ANHYDRIDES AS ACYLATING AGENTS IN LIPASE-CATALYZED STEREOSELECTIVE ESTERIFICATION OF RACEMIC ALCOHOLS [J].
BIANCHI, D ;
CESTI, P ;
BATTISTEL, E .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5531-5534
[3]  
BREIVA R, 1991, J CHEM SOC CHEM COMM, P1386
[4]   AMPLIFICATION OF ENANTIOSELECTIVITY IN BIOCATALYZED KINETIC RESOLUTION OF RACEMIC ALCOHOLS [J].
CHEN, CS ;
LIU, YC .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) :1966-1968
[5]   GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES [J].
CHEN, CS ;
SIH, CJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (06) :695-707
[6]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[7]  
FABER K, 1992, BIOTRANSFORMATIONS O
[8]   LIPASE-CATALYZED ENANTIOSELECTIVE SYNTHESIS OF NAPHTHYL TRIFLUOROMETHYL CARBINOLS AND THEIR CORRESPONDING NON-FLUORINATED COUNTERPARTS [J].
GASPAR, J ;
GUERRERO, A .
TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :231-238
[9]   SEQUENTIAL BIOCATALYTIC KINETIC RESOLUTIONS [J].
GUO, ZW ;
WU, SH ;
CHEN, CS ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4942-4945
[10]   RESOLUTION OF (+/-)-2-TETRADECYLOXIRANECARBOXYLIC ACID - ABSOLUTE-CONFIGURATION AND CHIRAL SYNTHESIS OF THE HYPOGLYCEMIC R ENANTIOMER AND BIOLOGICAL-ACTIVITY OF ENANTIOMERS [J].
HO, W ;
TARHAN, O ;
KIORPES, TC ;
TUTWILER, GF ;
MOHRBACHER, RJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (06) :1094-1097