PALLADIUM-CATALYZED CARBONYLATIVE [2+2] CYCLOADDITION FOR THE STEREOSELECTIVE SYNTHESIS OF EITHER CIS-3-ALKENYL OR TRANS-3-ALKENYL BETA-LACTAMS

被引：47

作者：

TANAKA, H ^{[1
]}

HAI, AKMA ^{[1
]}

SADAKANE, M ^{[1
]}

OKUMOTO, H ^{[1
]}

TORII, S ^{[1
]}

机构：

[1] OKAYAMA UNIV,FAC ENGN,DEPT APPL CHEM,OKAYAMA 700,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 11期

关键词：

D O I：

10.1021/jo00090a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new potential alkenylketene equivalent, prepared without use of a carboxylic acid or an activated derivative, has been exploited. Palladium-catalyzed carbonylation of an allyl phosphate in the presence of an imine and a tertiary amine under CO pressure (30 kg cm(-2)) stereoselectively gave either a cis-or trans-3-alkenyl beta-lactam in high yield. The stereochemical outcome strongly depends on the nature of the imine employed. Imines conjugated with a carbonyl such as a ketone or an ester stereoselectively produce cis-beta-lactams at room temperature, whereas imines unconjugated with a carbonyl group exclusively afford trans-beta-lactams at 70 degrees C.

引用

页码：3040 / 3046

页数：7

共 67 条

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