Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 16, Pages 2729-2734Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700700
Keywords
alkynyl 1,2-diketones; migration; N-heterocyclic carbenes; O-acylated allenolates; umpolung
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Funding
- strategic priority research program of the Chinese Academy of Sciences [XDB20000000]
- NSFC [21402199, 21502192]
- Chinese Recruitment Program of Global Experts
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The umpolung of alkynyl 1,2-diketones via N-heterocyclic carbene (NHC) catalysis was achieved for the first time, allowing the rapid access to a large variety of synthetically and pharmaceutically important alpha-pyrones under very mild conditions. A completely new NHC-catalyzed umpolung pattern involving an O-acylated allenolate as the key intermediate was proposed. Moreover, an unprecedented reaction pathway, featured by a series of group migrations and new bond formation, was postulated to demonstrate the formation of the products.
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