Domino Prins Cyclization of Enynols: Stereoselective Synthesis of Bicyclic Vinyl Fluorides

A fluoride‐induced termination of Prins cyclization has been observed using a tethered alkyne and stoichiometric amounts of AgSbF6 and found to generate a novel series of 6‐fluoro‐1‐aryl‐hexahydro‐1H‐isochromene derivatives in good yields with excellent selectivity. This is the first report of the s...

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Bibliographic Details
Published in:European journal of organic chemistry 2015-08, Vol.2015 (24), p.5389-5392
Main Authors: Venkateswarlu, Anipireddy, Kanakaraju, Marumudi, Kunwar, Ajit C., Rami Reddy, Yellala V., Reddy, Basi V. S.
Format: Article
Language:English
Subjects:
Acid catalysis
Alkynes
Cascade process
Cyclization
Domino reactions
Fluorides
Fluorine
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Summary:A fluoride‐induced termination of Prins cyclization has been observed using a tethered alkyne and stoichiometric amounts of AgSbF6 and found to generate a novel series of 6‐fluoro‐1‐aryl‐hexahydro‐1H‐isochromene derivatives in good yields with excellent selectivity. This is the first report of the synthesis of fluoro‐substituted oxabicycles. In this tandem process, three reactions occur in one‐pot to leading to installation of three contiguous stereocenters. A fluoride‐induced termination of the Prins cyclization observed with a tethered alkyne in the presence of AgSbF6 affords a novel series of 6‐fluoro‐1‐aryl‐hexahydro‐1H‐isochromene derivatives.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500689