Organic Letters
Organic Letters
5 years ago

Fluoride Anions in Self-Assembled Chiral Cage for the Enantioselective Protonation of Silyl Enol Ethers

Fluoride Anions in Self-Assembled Chiral Cage for the Enantioselective Protonation of Silyl Enol Ethers
Min-Jung Jung, Sang Yeon Park, Hailong Yan, Choong Eui Song, Sushovan Paladhi, Yidong Liu, B. Senthil Kumar
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01429

DOI: 10.1021/acs.orglett.7b01429

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