Diastereo- and Enantioselective (3 + 2) Cycloaddition of a New Aza-π-Allylpalladium Zwitterionic Intermediate
Résumé
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) γ-lactam cycloadducts could be formed with high level of diastero-and enantioselectivity.
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