TY - JOUR
T1 - Cycloadditions of 5-Vinyloxazolidine-2,4-diones
T2 - A Straightforward Access to the (Thio)hydantoin Scaffold
AU - Busicchia, Marc
AU - Roblin, Antoine
AU - Dubois, Carla
AU - Mekranter, Nagy
AU - Casaretto, Nicolas
AU - Archambeau, Alexis
N1 - Publisher Copyright:
© 2024 American Chemical Society.
PY - 2024/9/6
Y1 - 2024/9/6
N2 - 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.
AB - 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.
U2 - 10.1021/acs.joc.4c01315
DO - 10.1021/acs.joc.4c01315
M3 - Article
AN - SCOPUS:85201923846
SN - 0022-3263
VL - 89
SP - 12370
EP - 12377
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 17
ER -