Arylation of [6,6]-spiroacetal enol ethers: reactivity and rearrangement
Author(s)
Aumann, Kylee M
Healy, Peter C
Coster, Mark J
Griffith University Author(s)
Year published
2011
Metadata
Show full item recordAbstract
Attempts to selectively arylate [6,6]-spiroacetal enol ethers at the 2-position delivered unexpected results. Palladium-mediated arylation conditions afforded the double-Heck product, whereas reaction with benzenesulfinic acid resulted in a facile rearrangement into the corresponding 5-phenylsulfonyl-3,4,5,6-tetrahydrochromans, providing access to 5-aryl-3,4,5,6-tetrahydrochroman and hexahydrochroman derivatives.Attempts to selectively arylate [6,6]-spiroacetal enol ethers at the 2-position delivered unexpected results. Palladium-mediated arylation conditions afforded the double-Heck product, whereas reaction with benzenesulfinic acid resulted in a facile rearrangement into the corresponding 5-phenylsulfonyl-3,4,5,6-tetrahydrochromans, providing access to 5-aryl-3,4,5,6-tetrahydrochroman and hexahydrochroman derivatives.
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Journal Title
Tetrahedron Letters
Volume
52
Issue
10
Subject
Medicinal and biomolecular chemistry
Organic chemistry
Organic chemical synthesis