Department of Chemistry, School of Science, Xi'an Jiaotong University , Xi'an 710049, P. R. China.
Org Lett. 2017 Jun 16;19(12):3043-3046. doi: 10.1021/acs.orglett.7b00805. Epub 2017 May 26.
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 S1-type ring opening of the mechanism.
利用同共轭加成过程，开发了一种有机催化的环丙基酮的 Cloke-Wilson 重排反应，生成 2,3-二氢呋喃。以 1,4-二氮杂二环[2.2.2]辛烷为催化剂，在 DMSO 中于 120°C 进行的重排反应通常具有较高的产率、优异的区域选择性和广泛的底物范围。包括立体化学分析和中间体分离在内的对反应机理的研究支持 S1 型的开环机理。
