INVESTIGADORES
MEDRAN Noelia Soledad
artículos
Título:
Allenylboronic Acid Pinacol Ester: A Selective Partner for [4 + 2] Cycloadditions
Autor/es:
LABADIE, NATALIA; RAMOS MARCHENA, JUAN M.; MEDRÁN, NOELIA S.; PELLEGRINET, SILVINA C.
Revista:
ORGANIC LETTERS
Editorial:
AMER CHEMICAL SOC
Referencias:
Año: 2021 vol. 23 p. 5081 - 5085
ISSN:
1523-7060
Resumen:
We have studied the reaction of allenylboronic acid pinacol ester with cyclopentadiene with experimental and computational methods. The reaction occurred efficiently with complete Diels-Alder periselectivity and regioselectivity at the proximal double bond. The concerted mechanism for the observed transformation was computed to be favored over competitive addition to the distal double bond, [3,3]-sigmatropic rearrangements, and stepwise radical mechanism. This unprecedented Diels-Alder reaction enables the construction of synthetically versatile boron-substituted cycloadducts.
