Paper
Allenylboronic Acid Pinacol Ester: A Selective Partner for [4 + 2] Cycloadditions.
Published Jun 21, 2021 · DOI · N. Labadie, Juan M. Ramos Marchena, Noelia S. Medran
Organic letters
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Influential Citations
Abstract
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.
Allenylboronic acid pinacol ester efficiently reacts with cyclopentadiene, enabling the construction of versatile boron-substituted cycloadducts with complete Diels-Alder periselectivity and regioselectivity at the prox
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