Organocatalytic Cloke-Wilson Rearrangement: DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans

Jingfang Zhang; Yuhai Tang; Wen Wei; Yong Wu; Yang Li; Junjie Zhang; Yuansuo Zheng; Silong Xu

doi:10.1021/acs.orglett.7b00805

Organocatalytic Cloke-Wilson Rearrangement: DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans

Org Lett. 2017 Jun 16;19(12):3043-3046. doi: 10.1021/acs.orglett.7b00805. Epub 2017 May 26.

Authors

Jingfang Zhang¹, Yuhai Tang¹, Wen Wei¹, Yong Wu¹, Yang Li¹, Junjie Zhang¹, Yuansuo Zheng¹, Silong Xu¹

Affiliation

¹ Department of Chemistry, School of Science, Xi'an Jiaotong University , Xi'an 710049, P. R. China.

PMID: 28548502
DOI: 10.1021/acs.orglett.7b00805

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 S_N1-type ring opening of the mechanism.

Publication types

Research Support, Non-U.S. Gov't