Diastereoselectivity of the intramolecular attack on the electrophilic C=C bond of cyclopropene amides by benzylic nitrogen ylides is investigated. The readily available monobromo-cyclopropane amide starting materials were submitted to strongly basic conditions. A cyclopropene intermediate was formed via an E1cB-like mechanism and undergoes a facile rearrangement to form the ring closure product. Two methods of controlling the diastereoselectivity were considered. The effects of sterics were tested by varying one of the substituents on the amide nitrogen, and the electronic effects of adding substituents on the ring of the benzyl group were tested as well. Preliminary results of steric studies show successful ring closure, and some diastereoselectivites have been observed.

Five-membered ring closure via intramolecular nucleophilic attack by nitrogen ylides on C=C bond of cyclopropenes

251st National Meeting (2016)

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