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

作者：Aumann Kylee M; Healy Peter C; Coster Mark J^*

来源：Tetrahedron Letters, 2011, 52(10): 1070-1073.

DOI：10.1016/j.tetlet.2010.12.076

• Spiroacetal
• Enol ether
• Tetrahydrochroman
• Rearrangement
• Hexahydrochroman

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.

• 出版日期2011-3-9