PREPARATION OF ALPHA-METHYLENE AND ALPHA-ETHYLIDENE BETA-LACTAMS VIA THE ESTER ENOLATE IMINE CONDENSATION USING BETA-(DIALKYLAMINO) ESTERS AS STARTING MATERIALS - SCOPE AND SYNTHETIC APPLICATIONS

被引：36

作者：

ALCAIDE, B ^{[1
]}

ESTEBAN, G ^{[1
]}

MARTINCANTALEJO, Y ^{[1
]}

PLUMET, J ^{[1
]}

RODRIGUEZLOPEZ, J ^{[1
]}

MONGE, A ^{[1
]}

PEREZGARCIA, V ^{[1
]}

机构：

[1] UNIV COMPLUTENSE MADRID,FAC QUIM,DIFRACC RAYOS X LAB,E-28040 MADRID,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 26期

关键词：

D O I：

10.1021/jo00105a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, simple procedure for the preparation of appropriately substituted alpha-methylene and alpha-ethylidene beta-lactams via the ester enolate-imine condensation is described. The method is based on the use of lithium 3-(dialkylamino) ester enolates as synthetic equivalents of the corresponding acrylate alpha-anions. Thus, the reaction of lithium enolates of 3-(dialkylamino) esters with imines produced alpha-[(dialkylamino)alkyl] beta-lactams stereoselectively and in high yield. Upon dehydroamination the latter furnished a variety of alpha-alkylidene beta-lactams. The synthesis of 3-alkylidene-4-formyl-2-azetidinones is a particularly significant feature of this work. Preparation of functionalized alpha-keto beta-lactams and beta-lactam-furan hybrids through a dihydroxylation-oxidation process starting from different alpha-alkylidene derivatives is also described. In addition, reduction of various 4-functionalized (Z)- and (E)-3-ethylidene-2-azetidinones yielded the corresponding 3-ethylideneazetidines as advanced precursors of polyoximic acids.

引用

页码：7994 / 8002

页数：9

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