| Autor: |
Zhang J; Department of Chemistry, School of Science, Xi'an Jiaotong University , Xi'an 710049, P. R. China., Tang Y; Department of Chemistry, School of Science, Xi'an Jiaotong University , Xi'an 710049, P. R. China., Wei W; Department of Chemistry, School of Science, Xi'an Jiaotong University , Xi'an 710049, P. R. China., Wu Y; Department of Chemistry, School of Science, Xi'an Jiaotong University , Xi'an 710049, P. R. China., Li Y; Department of Chemistry, School of Science, Xi'an Jiaotong University , Xi'an 710049, P. R. China., Zhang J; Department of Chemistry, School of Science, Xi'an Jiaotong University , Xi'an 710049, P. R. China., Zheng Y; Department of Chemistry, School of Science, Xi'an Jiaotong University , Xi'an 710049, P. R. China., Xu S; Department of Chemistry, School of Science, Xi'an Jiaotong University , Xi'an 710049, P. R. China. |
| Abstrakt: |
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 S N 1-type ring opening of the mechanism. |
