Journal
NATURE COMMUNICATIONS
Volume 10, Issue -, Pages -Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/s41467-019-10651-w
Keywords
-
Categories
Funding
- National Key Research and Development Program of China [2017YFD0200500]
- NSFC [21722202, 21672069, 21871089]
- S&TCSM of Shanghai [18JC1415600]
- Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning
- National Program for Support of Top-notch Young Professionals
Ask authors/readers for more resources
The 1,2-dicarbonyl motif is vital to biomolecules, especially natural products and pharmaceuticals. Conventionally, 1,2-dicarbonyl compounds are prepared via an alpha-keto acyl chloride. Based on the methods used in nature, a transition-metal-free approach for the synthesis of an alpha-ketothioester reagent via the combination of an alpha-hydroxyl ketone, elemental sulfur and a benzyl halide is reported. Mechanistic studies demonstrate that the trisulfur radical anion and the alpha-carbon radical of the alpha-hydroxy ketone are involved in this transformation. The dicarbonylation of a broad range of amines and amino acids, and importantly, cross couplings with aryl borates to construct dicarbonyl-carbon bonds are realized under mild conditions by employing this stable and convenient alpha-ketothioester as a 1,2-dicarbonyl reagent. The dicarbonyl-containing drug indibulin and the natural product polyandrocarpamide C, which possess multiple heteroatoms and active hydrogen functional groups, can be efficiently prepared using the designed 1,2-dicarbonyl reagent.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available