THE ENOLATE-IMINE CONDENSATION USING LITHIUM DIANION OF 3-HYDROXYBUTANOATE AND N-ACYLALDIMINES - ENHANCED STEREOSELECTIVITY BY ADDED LITHIUM-CHLORIDE

被引：10

作者：

HATANAKA, M

PARK, OS

UEDA, I

机构：

[1] The Institute of Scientific and Industrial Research, Osaka University, Ibaraki, Osaka, 567, Mihogaoka

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 52期

关键词：

D O I：

10.1016/S0040-4039(00)97317-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enolate-imine condensation using the lithium dianion of 3-hydroxy-butanoate and N-acylaldimines gave the key intermediate for the preparation of (+)-thienamycin with improved stereoselection in the presence of lithium chloride.

引用

页码：7631 / 7632

页数：2

共 12 条

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[2] A FACILE ENTRY TO 3-(1-HYDROXYETHYL)-2-AZETIDINONES FROM METHYL(R)-3-HYDROXYBUTANOATE BASED ON THE ESTER ENOLATE-ALDIMINE CONDENSATION
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[4] STEREOSELECTIVE SYNTHESIS OF 3-(1-HYDROXYETHYL)-2-AZETIDINONES FROM 3-HYDROXYBUTYRATES
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[J]. TETRAHEDRON LETTERS, 1984, 25 (35) : 3779 - 3782
[5] ASYMMETRIC-SYNTHESIS OF (1'R,3R,4R)-4-ACETOXY-3-(1'-((TERT-BUTYLDIMETHYLSILYL)OXY)ETHYL)-2-AZETIDINONE AND OTHER 3-(1'-HYDROXYETHYL)-2-AZETIDINONES FROM (S)-(+)-ETHYL 3-HYDROXYBUTANOATE - FORMAL TOTAL SYNTHESIS OF (+)-THIENAMYCIN
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[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) : 1129 - 1135
[6] N-TRIMETHYLSILYL IMINES - APPLICATIONS TO THE SYNTHESIS OF BETA-LACTAMS
HA, DC
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[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (17) : 4819 - 4825
[7] A STEREOSELECTIVE APPROACH TO 1-BETA-METHYLCARBAPENEM ANTIBIOTIC STARTING FROM (R)-(-)-3-HYDROXYBUTYRIC ACID ESTER
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[J]. TETRAHEDRON LETTERS, 1987, 28 (01) : 83 - 86
[8] A STEREOCONTROLLED SYNTHESIS OF THE KEY INTERMEDIATE OF (+)-THIENAMYCIN FROM (R)-(-)-3-HYDROXYBUTYRIC ACID-ESTERS
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[J]. TETRAHEDRON LETTERS, 1987, 28 (01) : 69 - 72
[9] ACYCLIC STEREOSELECTION .7. STEREOSELECTIVE SYNTHESIS OF 2-ALKYL-3-HYDROXY CARBONYL-COMPOUNDS BY ALDOL CONDENSATION
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[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) : 1066 - 1081
[10] ESTER ENOLATE CLAISEN REARRANGEMENT - STEREOCHEMICAL CONTROL THROUGH STEREOSELECTIVE ENOLATE FORMATION
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[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) : 2868 - 2877

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