Lithium bromide-triethylamine induced cycloaddition of N-alkylidene 2-amino esters and amides to electron-deficient olefins with high regio-and stereoselectivity

O Tsuge, S Kanemasa, M Yoshioka

Index: Tsuge, Otohiko; Kanemasa, Shuji; Yoshioka, Manabu Journal of Organic Chemistry, 1988 , vol. 53, # 7 p. 1384 - 1391

Full Text: HTML

Citation Number: 134

Abstract

This suggested the use of a weaker base which is basic enough to deprotonate la but does not initiate the undesired polymerization. A combination of a metal halide and a tertiary amine was tried since this combination has been effectively employed in the olefination with base-labile 2-oxoalkylphosphonates or 2-phosphoryl esters-l'To our delight, the treatment of la with lithium bromide and triethylamine in dry THF at room temperature generated the ...