One-Pot Synthesis of Bicyclic β-Alkoxy Amides from Cyanohydrin Ethers

Abstract

In this manuscript we report that intramolecular Friedel-Crafts alkylation reactions of aryl-substituted alpha-alkoxy acylimines proceed in the presence of mild Lewis acids to afford bicyclic beta-alkoxy amides. The intermediate acylimines are prepared through cyanohydrin ether hydrozirconation and acylation of the resulting metalloimine, providing an operationally facile one pot protocol. A two-step variant of the procedure has also been developed to effect cyclizations from acylimines that undergo competitive tautomerization.