Cycloaddition vs. Michael Addition in the Metal Halide/Amine-Induced Reactions of α-(Alkylideneamino) Esters with Electron-Deficient Olefins
- 1 March 1989
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 62 (3) , 869-874
- https://doi.org/10.1246/bcsj.62.869
Abstract
The lithiated intermediate derived from methyl 2-(benzylideneamino)propanoate and lithium bromide/triethylamine undergoes cycloaddition and Michael addition with methyl acrylate. 1,3-Dipole character of the intermediate is suggested on the basis of the product ratios obtained under a variety of conditions. The reaction mechanism via a four-centered transition state is proposed.This publication has 8 references indexed in Scilit:
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