ON THE OPTIMIZATION OF PIG PANCREATIC LIPASE-CATALYZED MONOACETYLATION OF PROCHIRAL DIOLS

被引：30

作者：

BANFI, L ^{[1
]}

GUANTI, G ^{[1
]}

RIVA, R ^{[1
]}

机构：

[1] CNR,CTR STUDIO CHIM COMPOSTI CICLOALIFATICI & AROMATI,I-16132 GENOA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 06期

关键词：

D O I：

10.1016/0957-4166(95)00167-N

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The effect of various experimental variables (solvent, methodology of supportation on celite, presence of water, conversion and so on) on the rate and on the enantioselectivity of monoacetylation of some prochiral 2-substituted-1,3-propanediols with vinyl acetate catalyzed by crude PPL (pig pancreatic lipase) was analyzed. This study allowed to assess the best conditions for performing these transformations, providing an efficient methodology for the synthesis of valuable chiral building blocks with moderate amounts of inexpensive PPL, which can also be easily recycled.

引用

页码：1345 / 1356

页数：12

共 81 条

[1] ENZYMATIC ESTER HYDROLYSIS AND SYNTHESIS - 2 APPROACHES TO CYCLOALKANE DERIVATIVES OF HIGH ENANTIOMERIC PURITY [J].

ADER, U ;

BREITGOFF, D ;

KLEIN, P ;

LAUMEN, KE ;

SCHNEIDER, MP .

TETRAHEDRON LETTERS, 1989, 30 (14) :1793-1796

[2] TANDEM CYCLOADDITION-ENZYMATIC TRANSESTERIFICATION - AN ENANTIOSELECTIVE DIELS-ALDER REACTION EQUIVALENT [J].

ANDREU, C ;

MARCO, JA ;

ASENSIO, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3209-3210

[3] LIPASE-CATALYZED KINETIC RESOLUTION OF (+/-)-2-HYDROXYMETHYL-1,4-BENZODIOXANE [J].

ANTUS, S ;

GOTTSEGEN, A ;

KAJTAR, J ;

KOVACS, T ;

TOTH, TS ;

WAGNER, H .

TETRAHEDRON-ASYMMETRY, 1993, 4 (03) :339-344

[4] AN EFFICIENT ENANTIOSELECTIVE PREPARATION OF 2-SUBSTITUTED-3-HYDROXYPROPIONIC ACIDS VIA CHEMOENZYMATIC REACTION [J].

ATSUUMI, S ;

NAKANO, M ;

KOIKE, Y ;

TANAKA, S ;

OHKUBO, M ;

YONEZAWA, T ;

FUNABASHI, H ;

HASHIMOTO, J ;

MORISHIMA, H .

TETRAHEDRON LETTERS, 1990, 31 (11) :1601-1604

[5] LIPASE-CATALYZED IRREVERSIBLE TRANSESTERIFICATION USING ENOL ESTERS - RESOLUTION OF PROSTAGLANDIN SYNTHONS 4-HYDROXY-2-ALKYL-2-CYCLOPENTENONES AND INVERSION OF THE 4S ENANTIOMER TO THE 4R ENANTIOMER [J].

BABIAK, KA ;

NG, JS ;

DYGOS, JH ;

WEYKER, CL ;

WANG, YF ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3377-3381

[6] ASYMMETRIC-SYNTHESIS OF LOMETREXOL ((6R)-5,10-DIDEAZA-5,6,7,8-TETRAHYDROFOLIC ACID) [J].

BARNETT, CJ ;

WILSON, TM ;

WENDEL, SR ;

WINNINGHAM, MJ ;

DEETER, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (23) :7038-7045

[7]

BARNETT CJ, 1989, TETRAHEDRON LETT, V46, P6291

[8] 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

[9] ENZYMATIC-SYNTHESIS OF CHIRAL C4 BUILDING-BLOCKS FROM MESO-TARTARIC ACID [J].

BESTMANN, HJ ;

PHILIPP, UC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (01) :86-88

[10] ENZYMATIC RESOLUTION OF 2,3-EPOXYALCOHOLS, INTERMEDIATES IN THE SYNTHESIS OF THE GYPSY-MOTH SEX-PHEROMONE [J].

BIANCHI, D ;

CABRI, W ;

CESTI, P ;

FRANCALANCI, F ;

RAMA, F .

TETRAHEDRON LETTERS, 1988, 29 (20) :2455-2458

← 1 2 3 4 5 6 7 8 9 →