5 years ago

N-Heterocyclic Carbene-Catalyzed Umpolung of Alkynyl 1,2-Diketones

N-Heterocyclic Carbene-Catalyzed Umpolung of Alkynyl 1,2-Diketones
Shuang Yang, Xinqiang Fang, Guoxiang Zhang, Xiangwen Kong, Xiaozhi Liu
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 α-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.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700700

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