INVESTIGADORES
PELLEGRINET Silvina Carla
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.
