Organic Letters
Organic Letters
4 years ago

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

Organocatalytic Cloke–Wilson Rearrangement: DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans
Yuhai Tang, Silong Xu, Jingfang Zhang, Wen Wei, Yang Li, Junjie Zhang, Yong Wu, Yuansuo Zheng
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00805

DOI: 10.1021/acs.orglett.7b00805

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