Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 19, Pages 11926-11935Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01822
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Funding
- National Key Research and Development Program of China [2016YFA0602900]
- National Natural Science Foundation of China [21572071, 21420102003]
- Natural Science Foundation of Guangdong Province [2017A030313054]
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A copper-catalyzed [2 + 3] formal cyclization reaction between alpha-hydroxyl ketones and arylacetonitriles has been developed. The reaction outcome was ultimately dependent on the structure of the alpha-hydroxy ketones employed. Tertiary alpha-hydroxy ketones gave 3,4,5,5-tetrasubstituted butenolides as the sole products, while secondary alpha-hydroxy ketones furnished 2,4,5-trisubstituted oxazoles selectively. This method has many advantages, such as the use of easily available substrates, broad substrate scope, good functional tolerance, and milder reaction conditions.
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