Cycloadditions of 5-Vinyloxazolidine-2,4-diones: A Straightforward Access to the (Thio)hydantoin Scaffold
Marc Busicchia1, Antoine Roblin1, Carla Dubois1
1Laboratoire de Synthèse Organique, UMR 7652, CNRS, Ecole Polytechnique, ENSTA Paris, Institut Polytechnique de Paris, 91128 Palaiseau Cedex, France.
Abstract:
A palladium-catalyzed (3 + 2) cycloaddition between 5-vinyloxazolidine-2,4-diones (VOxD) and (thio)isocyanates is described. Under optimized conditions, an array of (thio)hydantoins was readily prepared, and an enantioselective version of this transformation was then studied. To illustrate the importance of this method, a concise synthesis of two bioactive compounds, nirvanol and mephenytoin, was carried out. This work emphasizes the synthetic potential of VOxD as useful precursors of zwitterionic aza-π-allylpalladiumII intermediates.
Related Concept Videos
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: MO Requirements for Thermal Activation
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
