Stereocontrolled Cyanohydrin Ether Synthesis through Chiral Brønsted Acid-Mediated Vinyl Ether Hydrocyanation
Vinyl ethers can be protonated to generate oxocarbenium ions that react with Me3SiCN to
form cyanohydrin alkyl ethers. Reactions that form racemic products proceed efficiently upon
conversion of the vinyl ether to an α-chloro ether prior to cyanide addition in a pathway that
proceeds through Brønsted acid-mediated chloride ionization. Enantiomerically enriched
products can be accessed by directly protonating the vinyl ether with a chiral Brønsted acid
to form a chiral ion pair. Me3SiCN acts as the nucleophile and PhOH serves as a …
form cyanohydrin alkyl ethers. Reactions that form racemic products proceed efficiently upon
conversion of the vinyl ether to an α-chloro ether prior to cyanide addition in a pathway that
proceeds through Brønsted acid-mediated chloride ionization. Enantiomerically enriched
products can be accessed by directly protonating the vinyl ether with a chiral Brønsted acid
to form a chiral ion pair. Me3SiCN acts as the nucleophile and PhOH serves as a …
[引用][C] Stereocontrolled Cyanohydrin Ether Synthesis through Chiral Brønsted Acid-Mediated Vinyl Ether Hydrocyanation
L Chunliang, S Xiaoge - 2013
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