Highly Selective Difluoromethylations of β-Keto Amides with TMSCF2Br under Mild Conditions
| Autor: | Yang Fu, Ting Zhao, Yanqin Hu, Shuaifei Wang, Pengli Chen, Yakun Wang, Conghui Zhang, Mingwei Zhang |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Difluorocarbene Base (chemistry) 010405 organic chemistry Organic Chemistry Enantioselective synthesis Alcohol 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Reagent Electrophile Selectivity |
| Zdroj: | Synlett. 32:1123-1130 |
| ISSN: | 1437-2096 0936-5214 |
| DOI: | 10.1055/a-1507-5878 |
| Popis: | Without employing any transition metal and other additives, efficient methods for selective difluoromethylations of β-keto amides with TMSCF2Br reagent have been developed under mild conditions. This protocol allows a convenient access to various α-difluoromethyl β-keto amides with excellent yields (up to 93%) and high carbon/oxygen (C/O) regioselectivities (up to 99:1). The C/O selectivity of β-keto amides could be easily reversed and controlled by simply changing the base. This protocol can be easily scaled-up and the C-difluoromethylation product could be reduced into CF2H-containing amino alcohol derivatives. Moreover, the first enantioselective electrophilic difluoromethylation of β-keto amides has been achieved by phase-transfer catalysis. |
| Databáze: | OpenAIRE |
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