The Diels-Alder reactions of boron-substituted furans with -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 diastereoisomer was obtained exclusively for the latter, while its C-3 counterpart showed variable / diastereoselectivities. Many strategies have been devised to improve the reactivity and selectivity of 3-boryl furans.
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