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Domino Synthesis of 2,3-Dialkylidenetetrahydrofurans via Tandem Prins Cyclization–Skeletal Reorganization

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journal contribution
posted on 25.07.2018 by Mizuki Kato, Akio Saito
A domino synthesis of 2,3-dialkylidenetetrahydrofurans based on Prins-type cyclization of 3,5-diynols and aldehydes is described. In the present reaction, skeletal reorganization of the Prins-cyclized intermediates proceeds via a ring-opening reaction followed by intramolecular (hemi)­acetalization of the resulting 4-en-1-yn-3-ones. Furthermore, a representative product undergoes a Diels–Alder reaction with dimethyl acetylenedicarboxylate (DMAD) to afford a highly substituted 2,3-dihydrobenzofuran.