Lewis Acid Coordinated Nitrile Oxide and Nitrile Imine 1,3-Dipoles. syn -Selective Cycloadditions to 2-(1-Hydroxyalkyl)acrylates

Abstract

Treatment of carbohydroximoyl chlorides with organometallics or carbohydrazonoyl chlorides with metal alkoxides or amides offers a new generation of Lewis acid-coordinated nitrile oxide and nitrile imine 1,3-dipoles, respectively. These 1,3-dipole/Lewis acid complexes undergo syn-selective cycloaddition reactions to 2-(1-hydroxyalkyl)acrylates through a chelated transition state, while free dipoles show anti-selectivities.