期刊
ORGANIC LETTERS
卷 19, 期 12, 页码 3043-3046出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00805
关键词
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资金
- National Natural Science Foundation of China [21402149, 21602167]
- Natural Science Basic Research Plan in Shaanxi Province of China [2015JQ2050, 2016JQ2019]
- China Postdoctoral Science Foundation [2014M5S0484, 2015T81013, 2015M580830]
- Shaanxi Province Postdoctoral Science Foundation
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 degrees 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.
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