SYNTHESIS OF 5S-(1-OXOALKYL AND ARYL)-2-PYRROLIDINONE DERIVATIVES

Citation
J. Deskus et al., SYNTHESIS OF 5S-(1-OXOALKYL AND ARYL)-2-PYRROLIDINONE DERIVATIVES, Synthetic communications, 28(9), 1998, pp. 1649-1659
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00397911
Volume
28
Issue
9
Year of publication
1998
Pages
1649 - 1659
Database
ISI
SICI code
0039-7911(1998)28:9<1649:SO5AAD>2.0.ZU;2-Q
Abstract
N-Benzyl pyroglutamate esters react with aryllithium reagents and meth yllithium to give moderate to good yields of 5-(1-oxoaryl) or 5-(1-oxo alkyl)-2-pyrrolidinone derivatives. The reaction proceeds without race mization, but is accompanied by formation of 5-(1-hydroxy-1-alkyl)-2-p yrrolidinone derivatives. This reaction gives very poor yields of keto ne products with most other alkyl organolithium reagents such as n-but yllithium. Grignard reagents react to give primarily the alcohol.