1. N-Heterocyclic Carbene-Catalyzed Umpolung of Alkynyl 1,2-Diketones.
- Author
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Kong, Xiangwen, Zhang, Guoxiang, Yang, Shuang, Liu, Xiaozhi, and Fang, Xinqiang
- Subjects
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HETEROCYCLIC compounds , *KETONES , *CHEMICAL reactions , *INTERMEDIATES (Chemistry) , *UMPOLUNG - Abstract
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. [ABSTRACT FROM AUTHOR]
- Published
- 2017
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