Abstract
A series of novel functionalized azetidinones containing the benzotriazole moiety were synthesized stereoselectively by a reaction of benzotriazolylacetic acid, aromatic amines, and Mukaiyama’s reagent in the presence of triethylamine in dichloromethane at ambient temperature. This transformation generates a four-membered lactam and presumably proceeds via in situ generation of benzotriazolylketene as a heteroarylketene. In contrast to the products obtained from the reaction of pyrrolylketene with imines in which cis -azetidinones were formed as major products, the generated benzotriazolylyketene reacted with imines forming the trans -lactams as major products.
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