Lewis Acid Coordinated Nitrile Oxide and Nitrile Imine 1,3-Dipoles. syn-Selective Cycloadditions to 2-(1-Hydroxyalkyl)acrylates
- 1 September 1993
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 66 (9) , 2685-2693
- https://doi.org/10.1246/bcsj.66.2685
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.This publication has 23 references indexed in Scilit:
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