N‐Heterocyclic Carbene‐Catalyzed Umpolung of Alkynyl 1, 2‐Diketones. Issue 16 (17th July 2017)

• Record Type: Journal Article
• Authors: Kong, Xiangwen; Zhang, Guoxiang; Yang, Shuang; Liu, Xiaozhi; Fang, Xinqiang
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 16(2017)
• Page Start: 2729
• Page End: 2734
• Publication Date: 2017-07-17
• Subjects: alkynyl 1, 2-diketones -- migration -- N-heterocyclic carbenes -- O-acylated allenolates -- umpolung; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201700700
• Languages: English
• ISSNs: 1615-4150

Abstract

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 :