Diels-Alder Reactions of Boron-Substituted Furans with N-Phenylmaleimide: Strategies for Tuning the Reactivity and
Federico Dezotti1, Noelia S Medrán1, Silvina C Pellegrinet1
1Instituto de Química Rosario (CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, Rosario 2000, Argentina.
Abstract:
The Diels-Alder reactions of boron-substituted furans with N-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 exo diastereoisomer was obtained exclusively for the latter, while its C-3 counterpart showed variable endo/exo diastereoselectivities. Many strategies have been devised to improve the reactivity and selectivity of 3-boryl furans.
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