Journal
ORGANIC LETTERS
Volume 16, Issue 17, Pages 4400-4403Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol502298a
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Funding
- NSFC [21272075]
- NCET [120178]
- DFMEC [20130076110023]
- Fok Ying Tung Education Foundation [141011]
- Shanghai Pujiang Program [12PJ1402500]
- program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning
- program for the Changjiang Scholar and Innovative Research Team in University
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An efficient and mild copper-catalyzed one-pot approach toward ynediones has been established. A variety of ynediones were constructed directly through oxidative coupling of alkyne with alpha-hydroxy ketone. Oxygen-oxidizing and neutral conditions in one-pot for a wide range of substrates including natural product derivatives make this transformation highly efficient and practical. On the basis of control experiments, in situ IR measurements, and isotopic labeling experiments, a plausible mechanism involving intermediate phenylglyoxal was drawn. Applications by synthesis of various heterocycles were also investigated.
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