Enantioselectivity and diastereoselectivity in the hydrolysis of acylals and structurally related esters of secondary alcohols with Candida rugosa lipase.

被引：18

作者：

Angelis, YS ^{[1
]}

Smonou, I ^{[1
]}

机构：

[1] Univ Crete, Dept Chem, Crete 71409, Greece

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(98)00256-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Comparative studies of enantioselectivities and diastereoselectivities in the hydrolysis reactions of acylals and 50:50 threo-erythro mixtures of the esters of related secondary alcohols with Candida rugosa lipase gave significant information about the reactivity order in the enzymatic hydrolysis of acylals. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：2823 / 2826

页数：4

相关论文

共 18 条

[1] Enzymatic hydrolysis of acylals. A promising route to chiral aldehydes [J].

Angelis, YS ;

Smonou, I .

TETRAHEDRON LETTERS, 1997, 38 (46) :8109-8112

[2] BIOTRANSFORMATIONS OF FLUORINATED SULFENYL AND SULFONYL COMPOUNDS [J].

BUCCIARELLI, M ;

FORNI, A ;

MORETTI, I ;

PRATI, F ;

TORRE, G ;

RESNATI, G ;

BRAVO, P .

TETRAHEDRON, 1989, 45 (23) :7505-7514

[3] 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

[4] STUDIES IN STEREOCHEMISTRY .5. PHENONIUM SULFONATE ION-PAIRS AS INTERMEDIATES IN THE INTRAMOLECULAR REARRANGEMENTS AND SOLVOLYSIS REACTIONS THAT OCCUR IN THE 3-PHENYL-2-BUTANOL SYSTEM [J].

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (09) :2129-2137

[5] A STRUCTURAL BASIS FOR THE CHIRAL PREFERENCES OF LIPASES [J].

CYGLER, M ;

GROCHULSKI, P ;

KAZLAUSKAS, RJ ;

SCHRAG, JD ;

BOUTHILLIER, F ;

RUBIN, B ;

SERREQI, AN ;

GUPTA, AK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3180-3186

[6] 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

[7] Iodine as acetylation catalyst in the preparation of 1,1-diacetates from aldehydes [J].

Deka, N ;

Kalita, DJ ;

Borah, R ;

Sarma, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1563-1564

[8] LIPASE-CATALYZED RESOLUTION OF ACYCLIC AMINO ALCOHOL PRECURSORS [J].

FOELSCHE, E ;

HICKEL, A ;

HONIG, H ;

SEUFERWASSERTHAL, P .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1749-1753

[9]

GREENZAI.P, 1971, BIOCHEMISTRY-US, V10, P1210

[10]

JONES JB, 1976, APPL BIOCH SYSTEMS O