Reaction of the lithio-derivative of methoxyallene with hydrazones. Part 1: Synthesis and transformation of α-allenyl hydrazines

V Breuil-Desvergnes, J Goré

Index: Breuil-Desvergnes, Valerie; Gore, Jacques Tetrahedron, 2001 , vol. 57, # 10 p. 1939 - 1950

Full Text: HTML

Citation Number: 26

Abstract

The lithio-derivative of methoxyallene reacts with aldehyde hydrazones leading to expected α-allenyl hydrazines when ether is the solvent of the reaction. The yields are good as well as the diastereoselectivity observed in the case of SAMP-hydrazones. These hydrazines are cleanly transformed to N-dialkylamino-3-methoxy-3-pyrrolines when they are reacted with n- BuLi in THF. These compounds are sometimes accompanied by the isomeric 4-methyl ...