Strain-Release-Driven Ring Opening of Vinyl-Azabicyclobutanes: A Platform for Allylic Functionalization

Résumé fourni par la source

Abstract A new class of azetidine-tethered allylic acetates was prepared via strain-release reactions of vinyl-ABB using acetic acid as nucleophile and used for Tsuji-Trost allylation. A broad range of primary and secondary alkylamines, sulfinates, active methylene compounds and azlactones were employed as nucleophiles to access tetrasubstituted alkylidene-azetidines in good yield. Also, in the absence of any nucleophile, acetate rearrangement was reported via the attack of the counter acetate anion from the less hindered site of the π-allyl-palladium species. Boc-deprotected tetrasubstituted alkylidene azetidine shows promising antibacterial activity against both Gram-positive and Gram-negative bacteria.

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