Diastereo- and Enantioselective (3+2) Cycloaddition of a New Palladium-Aza-Oxyallyl Intermediate

Cycloaddition of azaoxyallyl cations or other C-(C=O)-N synthon precursors is a well-established route towards lactams and other N-heterocycles but, despite the wide synthetic scope of this approach, enantioselective versions remain scarce. We herein report 5-vinyloxazolidine-2,4-diones (VOxD) as a suitable precursor of chiral palladium-aza-oxyallyl intermediates. In the presence of electrophilic alkenes, (3+2) -lactam cycloadducts could be formed with high level of diastero- and enantioselectivity.