Tetrahedron Letters

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

KM Aumann, PC Healy, MJ Coster

Index: Aumann, Kylee M.; Healy, Peter C.; Coster, Mark J. Tetrahedron Letters, 2011 , vol. 52, # 10 p. 1070 - 1073

Full Text: HTML

Citation Number: 2

Abstract

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.