Electronic and Steric Control in Regioselective Addition Reactions of Organolithium Reagents with Enaldimines

K Tomioka, Y Shioya, Y Nagaoka…

Index: Tomioka; Shioya; Nagaoka; Yamada Journal of Organic Chemistry, 2001 , vol. 66, # 21 p. 7051 - 7054

Full Text: HTML

Citation Number: 45

Abstract

A reaction mode of imines derived from naphthalene-1-carbaldehyde and acyclic α, β- unsaturated aldehydes with organolitium reagents was dependent on the characteristic nature of a substituent on the imine nitrogen atom. An imine having an electron-withdrawing aryl group on the nirtogen atom behaves as a 1, 2-directing imine toward organolithium reagents. In contrast, an imine bearing an alkyl or a bulky aryl group favors 1, 4-addition of ...