One-pot lipase-catalyzed synthesis of enantiopure secondary alcohols from carbonyl compounds: a new protocol for lipase-mediated resolution

被引：48

作者：

Kamal, A ^{[1
]}

Sandbhor, M ^{[1
]}

Ramana, KV ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Biotransformat Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(02)00170-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reduction of acetophenones with sodium borohydride in the presence of neutral alumina in hexane followed by enantioselective acylation catalyzed by Pseudomonas cepacia lipase has been achieved in one-pot. Further, immobilized lipase offered a high degree of selectivity with spontaneity. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：815 / 820

页数：6

相关论文

共 20 条

[1] 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

[2]

Drauz K., 1995, ENZYME CATALYSIS ORG

[3] IRREVERSIBLE AND HIGHLY ENANTIOSELECTIVE ACYLATION OF 2-HALO-1-ARYLETHANOLS IN ORGANIC-SOLVENTS CATALYZED BY A LIPASE FROM PSEUDOMONAS-FLUORESCENS [J].

HIRATAKE, J ;

INAGAKI, M ;

NISHIOKA, T ;

ODA, J .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6130-6133

[4] RESOLUTION OF SECONDARY ALCOHOLS BY ENZYME-CATALYZED TRANSESTERIFICATION IN ALKYL CARBOXYLATES AS THE SOLVENT [J].

JANSSEN, AJM ;

KLUNDER, AJH ;

ZWANENBURG, B .

TETRAHEDRON, 1991, 47 (36) :7645-7662

[5] ENZYMES IN ORGANIC-SYNTHESIS [J].

JONES, JB .

TETRAHEDRON, 1986, 42 (13) :3351-3403

[6] A facile preparation of (±)-β-hydroxy nitriles and their enzymatic resolution with lipases [J].

Kamal, A ;

Khanna, GBR .

TETRAHEDRON-ASYMMETRY, 2001, 12 (03) :405-410

[7] Chemoenzymatic synthesis of pyrrolo[2,1-b]quinazolinones:: Lipase-catalyzed resolution of vasicinone [J].

Kamal, A ;

Ramana, KV ;

Rao, MV .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (03) :997-1001

[8] Convenient enzymatic resolution of alcohols using highly reactive, nonharmful acyl donors, 1-ethoxyvinyl esters [J].

Kita, Y ;

Takebe, Y ;

Murata, K ;

Naka, T ;

Akai, S .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01) :83-88

[9]

Koskinen AMP., 1996, Enzymatic reactions in organic media, DOI DOI 10.1007/978-94-011-0611-5_11

[10] ENZYMIC PREPARATION OF ENANTIOMERICALLY PURE SECONDARY ALCOHOLS - ESTER SYNTHESIS BY IRREVERSIBLE ACYL TRANSFER USING A HIGHLY SELECTIVE ESTER HYDROLASE FROM PSEUDOMONAS SP - AN ATTRACTIVE ALTERNATIVE TO ESTER HYDROLYSIS [J].

LAUMEN, K ;

BREITGOFF, D ;

SCHNEIDER, MP .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (22) :1459-1461