Preparation and Electrophilic Cyclization of Multisubstituted Dienamides Leading to Cyclic Iminoethers

Stereodefined multisubstituted dienamides could be concisely prepared in high yields by direct
addition of 1-lithiobutadiene derivatives to both N-aryl and N-alkyl isocyanates. Electrophilic
cyclization of these dienamides was achieved to generate substituted cyclic iminoethers in excellent
yields with perfect selectivity. When treated with 12 N aqueous HCl, dienamides underwent efficient
and selective electrophilic cyclization to afford cyclic imidate derivatives. When treated with NBS,
monobrominated or double-brominated cyclic iminoethers were formed.