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

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...

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Bibliographic Details
Published in:Organic letters 2018-08, Vol.20 (15), p.4709-4712
Main Authors: Kato, Mizuki, Saito, Akio
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02114