NITRILE OXIDES IN MEDICINAL CHEMISTRY .5. LIPASE PS-CATALYZED RESOLUTION OF A SET OF HETEROCYCLIC-DERIVATIVES

被引：22

作者：

CARREA, G ^{[1
]}

DEAMICI, M ^{[1
]}

DEMICHELI, C ^{[1
]}

LIVERANI, P ^{[1
]}

CARNIELLI, M ^{[1
]}

RIVA, S ^{[1
]}

机构：

[1] UNIV TRIESTE, DIPARTIMENTO SCI FARMACEUT, I-34127 TRIESTE, ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 05期

关键词：

D O I：

10.1016/S0957-4166(00)80155-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Lipase from Pseudomonas cepacia (lipase PS) catalyzed the hydrolysis of a series of butyrates of racemic primary alcohols carrying a DELTA2-isoxazoline or an isoxazolidin-3-one nucleus. Within this set of compounds, the enantiopreference of the catalyst can be accounted for by a rule recently proposed for lipase PS-catalyzed resolution of secondary alcohols. Nevertheless much work needs to be done in order to become predictive of the degree of enantioselectivity and of the relative reaction rates.

引用

页码：1063 / 1072

页数：10

共 24 条

[11] SYNTHESIS AND PHARMACOLOGICAL INVESTIGATION OF CHOLINERGIC LIGANDS STRUCTURALLY RELATED TO MUSCARONE [J].

DEAMICI, M ;

DEMICHELI, C ;

GRANA, E ;

RODI, R ;

ZONTA, F ;

SANTAGOSTINOBARBONE, MG .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1989, 24 (02) :171-177

[12] NITRILE OXIDES IN MEDICINAL CHEMISTRY .2. SYNTHESIS OF THE 2 ENANTIOMERS OF DIHYDROMUSCIMOL [J].

DEAMICI, M ;

DEMICHELI, C ;

MISANI, V .

TETRAHEDRON, 1990, 46 (06) :1975-1986

[13] 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

[14]

GRANA E, COMMUNICATION

[15] INDOLE SYNTHESES WITH ORTHO-TOLYL ISOCYANIDE - 3-ACYLINDOLES AND 2-SUBSTITUTED INDOLES [J].

ITO, Y ;

KOBAYASHI, K ;

SAEGUSA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (12) :2030-2032

[16] A RULE TO PREDICT WHICH ENANTIOMER OF A SECONDARY ALCOHOL REACTS FASTER IN REACTIONS CATALYZED BY CHOLESTEROL ESTERASE, LIPASE FROM PSEUDOMONAS-CEPACIA, AND LIPASE FROM CANDIDA-RUGOSA [J].

KAZLAUSKAS, RJ ;

WEISSFLOCH, ANE ;

RAPPAPORT, AT ;

CUCCIA, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2656-2665

[17]

KRAUS GA, 1980, J ORG CHEM, V45, P4821

[18] A STUDY OF THE MIXED TISCHTSCHENKO REACTION [J].

LIN, I ;

DAY, AR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (20) :5133-5135

[19] THE REACTIONS OF PRIMARY NITROPARAFFINS WITH ISOCYANATES [J].

MUKAIYAMA, T ;

HOSHINO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (20) :5339-5342

[20]

SCHWAB W, 1981, ANGEW CHEM, V39, P578

← 1 2 3 →