Synthesis of 3-benzylidenetetrahydrofurans: Tf2O-catalyzed hydroxylation/cyclization of cyclopropanemethanols with DMSO

A formal hydroxylation/cyclization of cyclopropanemethanols with DMSO is described, which involves isomerization and cyclization under Tf2O catalysis. This reaction undergoes ring-opening of the cyclopropane moiety to generate homoallylic alcohols, which react with DMSO to produce 3-benzylidenetetra...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-12, Vol.56 (100), p.15627-15630
Main Authors: Qi, Zhenjie, Wang, Hongchen, Ren, Yi, Niu, Yanning, Jiang, Yong, Rulong Yan
Format: Article
Language:English
Subjects:
Alcohols
Chemical synthesis
Cyclopropane
Hydroxylation
Isomerization
Ring opening
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Summary:A formal hydroxylation/cyclization of cyclopropanemethanols with DMSO is described, which involves isomerization and cyclization under Tf2O catalysis. This reaction undergoes ring-opening of the cyclopropane moiety to generate homoallylic alcohols, which react with DMSO to produce 3-benzylidenetetrahydrofurans. With various substituted groups on cyclopropanemethanols the reactions proceed smoothly and the desired 3-benzylidenetetrahydrofurans are obtained in moderate to good yields.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc07002e