Diels–Alder Reactions of Boron-Substituted Furans with <i>N</i>-Phenylmaleimide: Strategies for Tuning the Reactivity and Selectivity
The Diels-Alder reactions of boron-substituted furans with <i>N</i>-phenylmaleimide have been investigated experimentally and computationally. In contrast to previous results with maleic anhydride, in this case potassium 3-furanyltrifluoroborate and the analogue at C-2 reacted efficiently, giving the [4 + 2] cycloadducts at room temperature with high yields. The <i>exo</i> diastereoisomer was obtained exclusively for the latter, while its C-3 counterpart showed variable <i>endo</i>/<i>exo</i> diastereoselectivities. Many strategies have been devised to improve the reactivity and selectivity of 3-boryl furans.
Authors
- Noelia S. Medrán (ORCID: https://orcid.org/0000-0001-8284-4511)
- Federico Dezotti
- Silvina C. Pellegrinet (ORCID: https://orcid.org/0000-0001-6854-7377)
Institutions
- National University of Rosario (AR)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-01-10
- DOI
- https://doi.org/10.1021/acs.joc.4c02671
- Citations
- 1
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- Universidad Nacional de Rosario
- Consejo Nacional de Investigaciones Científicas y Técnicas
- Agencia Santafesina de Ciencia, Tecnología e Innovación
- Agencia Nacional de Promoción Científica y Tecnológica