ENZYME-MEDIATED ENANTIOSELECTIVE HYDROLYSIS OF CYCLIC CARBONATES

被引：33

作者：

MATSUMOTO, K ^{[1
]}

FUWA, S ^{[1
]}

KITAJIMA, H ^{[1
]}

机构：

[1] FUKUI UNIV,FAC ENGN,DEPT APPL CHEM & BIOTECHNOL,FUKUI 910,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 36期

关键词：

D O I：

10.1016/0040-4039(95)01300-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enzyme-mediated enantioselective hydrolysis of cyclic carbonates is disclosed. Racemic 4-(2-benzyloxy)ethyl-1,3-dioxolan-2-one (1a) was enantioselectively hydrolyzed by porcine pancreas lipase (PPL) to give optically active (R)-1a and (S)-4-benzyloxybutane-1,2-diol (2a). PPL also catalyzed the hydrolysis of seveal five-membered cyclic carbonates with high enatioselectivity.

引用

页码：6499 / 6502

页数：4

共 21 条

[1] ENZYMATIC RESOLUTION OF 1,2-DIOLS - PREPARATION OF OPTICALLY PURE DROPROPIZINE [J].

BIANCHI, D ;

BOSETTI, A ;

CESTI, P ;

GOLINI, P .

TETRAHEDRON LETTERS, 1992, 33 (22) :3231-3234

[2] AMINE ASSISTED ENZYMATIC ESTERIFICATION OF 1,2-DIOL MONOTOSYLATES [J].

BOAZ, NW ;

ZIMMERMAN, RL .

TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :153-156

[3] ENZYME-CATALYZED DESYMMETRIZATION OF MESO-SKIPPED POLYOLS TO USEFUL CHIRAL BUILDING-BLOCKS [J].

BONINI, C ;

RACIOPPI, R ;

VIGGIANI, L .

TETRAHEDRON-ASYMMETRY, 1993, 4 (05) :793-805

[4] A SAFE AND EFFICIENT METHOD FOR CONVERSION OF 1,2-DIOLS AND 1,3-DIOLS TO CYCLIC CARBONATES UTILIZING TRIPHOSGENE [J].

BURK, RM ;

ROOF, MB .

TETRAHEDRON LETTERS, 1993, 34 (03) :395-398

[5] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].

CHEN, CS ;

FUJIMOTO, Y ;

GIRDAUKAS, G ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299

[6] MICROBIOLOGICAL TRANSFORMATIONS .27. THE 1ST EXAMPLES FOR PREPARATIVE-SCALE ENANTIOSELECTIVE OR DIASTEREOSELECTIVE EPOXIDE HYDROLYZES USING MICROORGANISMS - AN UNEQUIVOCAL ACCESS TO ALL 4 BISABOLOL STEREOISOMERS [J].

CHEN, XJ ;

ARCHELAS, A ;

FURSTOSS, R .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5528-5532

[7] REGIOSELECTIVE AND ENANTIOSELECTIVE ESTERIFICATIONS OF POLYOXYGENATED COMPOUNDS CATALYZED BY LIPASES [J].

HERRADON, B ;

CUETO, S ;

MORCUENDE, A ;

VALVERDE, S .

TETRAHEDRON-ASYMMETRY, 1993, 4 (05) :845-864

[8] LIPASE-CATALYZED ENANTIOSELECTIVE TRANSESTERIFICATION OF O-TRITYL 1,2-DIOLS - PRACTICAL SYNTHESIS OF (R)-TRITYLGLYCIDOL [J].

KIM, MJ ;

CHOI, YK .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1605-1607

[9] SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (+)-8-HYDROXY-HEXADECANOIC ACID, AN ENDOGENOUS INHIBITOR FOR SPORE GERMINATION IN LYGODIUM-JAPONICUM [J].

MASAOKA, Y ;

SAKAKIBARA, M ;

MORI, K .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1982, 46 (09) :2319-2324

[10] SYNTHESIS OF ACYCLIC POLYOL DERIVATIVES VIA ENZYME-MEDIATED ALDOL REACTION [J].

MATSUMOTO, K ;

SHIMAGAKI, M ;

NAKATA, T ;

OISHI, T .

TETRAHEDRON LETTERS, 1993, 34 (31) :4935-4938

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