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Arylation of [6,6]-spiroacetal enol ethers: reactivity and rearrangement

✍ Scribed by Kylee M. Aumann; Peter C. Healy; Mark J. Coster

Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
674 KB
Volume
52
Category
Article
ISSN
0040-4039

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✦ Synopsis

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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## Abstract The absolute configurations of three 6,7‐oxygenated acetylenic spiroacetal enol ethers were determined by using the kinetic method of Horeau. The results were confirmed by the circular dichroism of the compounds in correlation with the corresponding 6,7‐epoxide.