HIGHLY ENANTIOSELECTIVE REDUCTION OF MESO-CYCLIC-1,2-DICARBOXIMIDES - ASYMMETRIC-SYNTHESIS OF BICYCLIC 2-PYRROLIDINONE AND ITS 5-HYDROXY CONGENER

被引：20

作者：

MATSUKI, K ^{[1
]}

INOUE, H ^{[1
]}

ISHIDA, A ^{[1
]}

TAKEDA, M ^{[1
]}

NAKAGAWA, M ^{[1
]}

HINO, T ^{[1
]}

机构：

[1] CHIBA UNIV,FAC PHARMACEUT SCI,INAGE KU,CHIBA 263,JAPAN

来源：

HETEROCYCLES | 1993年 / 36卷 / 05期

关键词：

D O I：

10.3987/COM-92-6307

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclic 5-hydroxy-2-pyrrolidinones (2a - f) were synthesized with high enantioselectivity by the reduction of meso underbar-cyclic- 1,2-dicarboximides (1a - f) with lithium aluminum hydride (LiAlH4)- methanol (MeOH)- 1,1'-bi-2-naphthol complex (BINAL-H). Treatment of 2a - f with triethylsilane (Et3SiH) and trifluoroacetic acid(CF3CO2H) gave optically active 2-pyrrolidinones (3a - f) in quantitative yields. For the absolute configuration correlation, 2a - d were converted into known lactones (4a - d).

引用

页码：937 / 940

页数：4

共 14 条

[1]

ARAI Y, 1992, TETRAHEDRON-ASYMMETR, V3, P535

[2] STEREOSELECTIVE SYNTHESIS OF A TRANS-OCTAHYDROINDOLE DERIVATIVE, PRECURSOR OF TRANDOLAPRIL (RU-44 570), AN INHIBITOR OF ANGIOTENSIN CONVERTING ENZYME [J].

BRION, F ;

MARIE, C ;

MACKIEWICZ, P ;

ROUL, JM ;

BUENDIA, J .

TETRAHEDRON LETTERS, 1992, 33 (34) :4889-4892

[3] ASYMMETRIC TOTAL SYNTHESIS OF THE MACROLIDES BREFELDIN-A AND 7-EPI-BREFELDIN-A [J].

GAIS, HJ ;

LIED, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (02) :145-146

[4] ENANTIOSELECTIVE AND ENANTIOCONVERGENT SYNTHESES OF BUILDING-BLOCKS FOR THE TOTAL SYNTHESIS OF CYCLOPENTANOID NATURAL-PRODUCTS [J].

GAIS, HJ ;

LUKAS, KL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (02) :142-143

[5]

GAIS HJ, 1986, LIEBIGS ANN CHEM, P687

[6] ENZYMES IN ORGANIC-SYNTHESIS .24. PREPARATIONS OF ENANTIOMERICALLY PURE CHIRAL LACTONES VIA STEREOSPECIFIC HORSE LIVER ALCOHOL-DEHYDROGENASE CATALYZED OXIDATIONS OF MONOCYCLIC MESO DIOLS [J].

JAKOVAC, IJ ;

GOODBRAND, HB ;

LOK, KP ;

JONES, JB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (17) :4659-4665

[7] CONFORMATIONAL EQUILIBRIA IN CIS-1,2,3,6-TETRAHYDROPHTHALIC ANHYDRIDE SERIES [J].

LARTER, RM ;

CRAIG, RER ;

CRAIG, AC ;

MUNDY, BP .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (07) :1259-1261

[8] HIGHLY SELECTIVE FORMATION OF CIS-SUBSTITUTED HYDROXYLACTAMS VIA AUXILIARY-CONTROLLED REDUCTION OF IMIDES [J].

MILLER, SA ;

CHAMBERLIN, AR .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2502-2504

[9] ENANTIOMERICALLY PURE POLYHYDROXYLATED ACYLIMINIUM IONS - SYNTHESIS OF THE GLYCOSIDASE INHIBITORS (-)-SWAINSONINE AND (+)-CASTANOSPERMINE [J].

MILLER, SA ;

CHAMBERLIN, AR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8100-8112

[10] AN ASYMMETRIC-SYNTHESIS OF BICYCLIC LACTONES AND ITS APPLICATION TO THE ASYMMETRIC-SYNTHESIS OF (1R,3S)-CIS-CHRYSANTHEMIC ACID [J].

MUKAIYAMA, T ;

YAMASHITA, H ;

ASAMI, M .

CHEMISTRY LETTERS, 1983, (03) :385-388

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