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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Preparation and electrophilic cyclization of multisubstituted dienamides leading to cyclic iminoethers
Congyang Wang1, Jiang Lu, Guoliang Mao
1Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.
Abstract:
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.
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