Fluoride Anions in Self-Assembled Chiral Cage for the Enantioselective Protonation of Silyl Enol Ethers
| Autor: | Sushovan Paladhi, Hailong Yan, Min-Jung Jung, B. Senthil Kumar, Sang Yeon Park, Yidong Liu, Choong Eui Song |
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| Rok vydání: | 2017 |
| Předmět: |
Silylation
Trimethylsilyl 010405 organic chemistry Organic Chemistry Enantioselective synthesis Protonation 010402 general chemistry 01 natural sciences Biochemistry Enol 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Organic chemistry Physical and Theoretical Chemistry Fluoride Tetralones |
| Zdroj: | Organic Letters. 19:3279-3282 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.7b01429 |
| Popis: | The potential of Song's chiral oligoethylene glycols (oligoEGs) as catalysts was explored in the enantioselective protonation of trimethylsilyl enol ethers in combination with alkali metal fluoride (KF and CsF) and in the presence of a proton source. Highly enantioselective protonations of various silyl enol ethers of α-substituted tetralones were achieved, producing chiral α-substituted tetralones in full conversion and with up to 99% ee. The established protocol was successfully extended to the synthesis of biologically relevant chiral α-substituted chromanone and thiochromanone derivatives. |
| Databáze: | OpenAIRE |
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