1.
Org Lett
; 23(13): 5081-5085, 2021 Jul 02.
Artigo
em Inglês
| MEDLINE
| ID: mdl-34151574
RESUMO
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.