1-Ethoxyvinyl acetate as a novel, highly reactive, and reliable acyl donor for enzymatic resolution of alcohols

被引：40

作者：

Kita, Y

Takebe, Y

Murata, K

Naka, T

Akai, S

机构：

[1] Faculty of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565, 1-6, Yamada-oka

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 41期

关键词：

D O I：

10.1016/0040-4039(96)01658-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Ethoxyvinyl acetate 3 was found to be a high performance acyl donor for enzymatic resolution of alcohols featuring that (i) 3 shows high reactivity and high selectivity comparable to the most widely used vinyl acetate 1 and (ii) reaction of 3 generates low reactivity ethyl acetate 6 as a single side product, while that of 1 releases unfavorable acetaldehyde 4. Copyright (C) 1996 Elsevier Science Ltd

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页码：7369 / 7372

页数：4

相关论文

共 31 条

[1] ENZYMATIC ESTERIFICATION AND DE-ESTERIFICATION OF CARBOHYDRATES - SYNTHESIS OF A NATURALLY-OCCURRING RHAMNOPYRANOSIDE OF P-HYDROXYBENZALDEHYDE AND A SYSTEMATIC INVESTIGATION OF LIPASE-CATALYZED ACYLATION OF SELECTED ARYLPYRANOSIDES [J].

BASHIR, NB ;

PHYTHIAN, SJ ;

REASON, AJ ;

ROBERTS, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (18) :2203-2222

[2] IMMUNIZATION OF LIPASE AGAINST ACETALDEHYDE EMERGING IN ACYL TRANSFER-REACTIONS FROM VINYL-ACETATE [J].

BERGER, B ;

FABER, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (17) :1198-1200

[3] 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

[4] 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

[5] ENZYMATIC-REACTIONS IN ORGANIC-SYNTHESIS .2. ESTER INTERCHANGE OF VINYL ESTERS [J].

DEGUEILCASTAING, M ;

DEJESO, B ;

DROUILLARD, S ;

MAILLARD, B .

TETRAHEDRON LETTERS, 1987, 28 (09) :953-954

[6]

FABER K, 1992, SYNTHESIS-STUTTGART, P895

[7]

FABER K, 1992, BIOTRANSFORMATIONS O, P248

[8] OXIME ESTERS AS NOVEL IRREVERSIBLE ACYL TRANSFER AGENTS FOR LIPASE CATALYSIS IN ORGANIC MEDIA [J].

GHOGARE, A ;

KUMAR, GS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (20) :1533-1535

[9]

GOTOR V, 1992, SYNTHESIS-STUTTGART, P626

[10] AN IMPROVED PROCEDURE FOR REGIOSELECTIVE ACYLATION OF CARBOHYDRATES - NOVEL ENZYMATIC ACYLATION OF ALPHA-D-GLUCOPYRANOSE AND METHYL ALPHA-D-GLUCOPYRANOSIDE [J].

GOTOR, V ;

PULIDO, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02) :491-492

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