Tethered Aza-Wacker Cyclization Reactions with Unusual N-Alkoxy Carbamates

Substrates with N-alkoxy carbamate “heads” and olefin “tails” can be productively cyclized into 1,3-oxazinan-2- one products bearing pendant alkenes. Our reaction protocol is operationally simple and involves heating substrate with a mixture of Pd (II) and Cu (II) salts in CH3CN under 1 atm of O2. We hypothesize that an aza-Wacker mechanism is operative, based on prior art and our own experience with this reaction class. An array of substrates is compatible, and the heterocyclic products are amenable to further transformations.