Journal
ORGANIC LETTERS
Volume 23, Issue 13, Pages 5081-5085Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01609
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The reaction between allenylboronic acid pinacol ester and cyclopentadiene showed efficient, selective, and regioselective characteristics. The concerted mechanism was found to be favored over competitive addition, [3,3]-sigmatropic rearrangements, and stepwise radical mechanism, providing a new pathway for the construction of versatile boron-substituted cycloadducts.
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.
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