SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF THE TIN ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES - A COMPARISON BETWEEN TITANIUM AND TIN ENOLATES

被引：21
作者：
ANNUNZIATA, R
BENAGLIA, M
CINQUINI, M
COZZI, F
RAIMONDI, L
机构：
[1] UNIV MILAN,CTR CNR,I-20133 MILAN,ITALY
[2] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY
来源：
TETRAHEDRON | 1994年 / 50卷 / 19期
关键词：
D O I：
10.1016/S0040-4020(01)85649-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Addition of tricthylamine to a mixture of 2-pyridylthioesters and SnCl4 or SnBr4 affords the corresponding tin(IV) enolates that add to imines to give beta-lactams in fair to good yields and with various degree of trans/cis stereoselectivity. Examples of highly diastereofacially selective reactions carried out on a chiral thioester and on a chiral imine are also reported. The results are compared with those obtained in the condensations promoted by TiCl4 and TiBr4.
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页码：5821 / 5828
页数：8
相关论文
共 18 条
[1]   SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES - INFLUENCE OF THE IMINE STRUCTURE ON THE TRANS/CIS STEREOSELECTIVITY [J].
ANNUNZIATA, R ;
BENAGLIA, M ;
CINQUINI, M ;
COZZI, F ;
PONZINI, F ;
RAIMONDI, L .
TETRAHEDRON, 1994, 50 (09) :2939-2948
[2]   STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES BEARING A CHIRAL AUXILIARY [J].
ANNUNZIATA, R ;
BENAGLIA, M ;
CINQUINI, M ;
COZZI, F ;
RAIMONDI, L .
TETRAHEDRON LETTERS, 1993, 34 (43) :6921-6924
[3]   STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYL THIOESTERS WITH IMINES [J].
ANNUNZIATA, R ;
CINQUINI, M ;
COZZI, F ;
COZZI, PG .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4155-4162
[4]   STEREOSELECTIVE SYNTHESIS OF AZETIDIN-2-ONES, PRECURSORS OF BIOLOGICALLY-ACTIVE SYN-3-AMINO-2-HYDROXYBUTANOIC ACIDS [J].
ANNUNZIATA, R ;
BENAGLIA, M ;
CINQUINI, M ;
COZZI, F ;
PONZINI, F .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4746-4748
[5]  
ANNUNZIATA R, 1993, GAZZ CHIM ITAL, V123, P181
[6]  
BROWN MJ, 1989, HETEROCYCLES, V29, P2225
[7]   THE LEWIS ACID COMPLEXES OF ALPHA,BETA-UNSATURATED CARBONYL AND NITRILE COMPOUNDS .1. A NUCLEAR MAGNETIC-RESONANCE STUDY [J].
CHILDS, RF ;
MULHOLLAND, DL ;
NIXON, A .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (06) :801-808
[8]   MILD AND CONVENIENT ONE-POT SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES [J].
CINQUINI, M ;
COZZI, F ;
COZZI, PG ;
CONSOLANDI, E .
TETRAHEDRON, 1991, 47 (41) :8767-8774
[9]   SYNTHESIS OF TRANS-1-P-METHOXYPHENYL-3-ACETOXY-4-PHENYLAZETIDIN-2-ONE - A KEY STARTING BETA-LACTAM FOR 2'-EPI-TAXOL [J].
ENDO, M ;
DROGHINI, R .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (11) :2483-2486
[10]   ENANTIOSELECTIVE MICHAEL REACTIONS - DIASTEREOSELECTIVE REACTIONS OF CHLOROTITANIUM ENOLATES OF CHIRAL N-ACYLOXAZOLIDINONES WITH REPRESENTATIVE ELECTROPHILIC OLEFINS [J].
EVANS, DA ;
BILODEAU, MT ;
SOMERS, TC ;
CLARDY, J ;
CHERRY, D ;
KATO, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5750-5752
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