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

Author:
Kato, Mizuki, Saito, Akio
Source:
Organic letters 2018 v.20 no.15 pp. 4709-4712
ISSN:
1523-7052
Subject:
aldehydes, chemical reactions, chemical structure
Abstract:
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.
Agid:
6084334