Jingfang Zhang, Yuhai Tang, Wentao Wei
May 26, 2017
Citations
0
Influential Citations
60
Citations
Journal
Organic letters
Abstract
An organocatalytic Cloke-Wilson rearrangement of cyclopropyl ketones to 2,3-dihydrofurans is exploited utilizing the homoconjugate addition process. With 1,4-diazabicyclo[2.2.2]octane as the catalyst, the rearrangement in DMSO at 120 °C proceeded in generally high yields, exclusive regioselectivity, and a broad substrate scope. An examination of the mechanism including stereochemical analysis and intermediate isolation supports an SN1-type ring opening of the mechanism.