2024-11-192024-11-192018-10-02Pisano, P. L. and Pellegrinet, S. C. (2018). Alkylhalovinylboranes: a new class of Diels-Alder dienophiles. RSC Advances, 12(59), 33864-33871. https://doi.org/10.1039/C8RA07089J2046-2069https://hdl.handle.net/2133/28159The Diels–Alder reactions of alkylhalovinylboranes have been investigated theoretically and experimentally. Alkylhalovinylboranes presented higher reactivity than the corresponding dialkylvinylboranes. Although endo/exo selectivities were high for the reactions with cyclopentadiene, facial selectivities for the chiral analogues were low. Our results demonstrate that the replacement of an alkyl group on the boron atom by a halogen increases the dienophilicity considerably.1-8enopenAccessAlkylhalovinylboranesDiels Alder reactionDienophilesOrganoboron compoundsBoronCyclopentanesHalogensAlkylRational designarticuloPisano, Pablo LuisPellegrinet, Silvina CarlaUniversidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y FarmacéuticasAttribution-NonCommercial 4.0 International