Thiourea-catalyzed enantioselective cyanosilylation of ketones.
The new chiral amino thiourea catalyst 3d promotes the highly enantioselective cyanosilylation of a wide variety of ketones. The hindered tertiary amine substituent plays a crucial role with regard to both stereoinduction and reactivity, suggesting a cooperative mechanism involving electrophile activation by thiourea and nucleophile activation by the amine.
Fuerst
Douglas E
DE
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02318, USA.
Jacobsen
Eric N
EN
D002384:Catalysis; D003486:Cyanides / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
D003486:Cyanides; D007659:Ketones; D014297:Trimethylsilyl Compounds; C058010:trimethylsilyl cyanide; D013890:Thiourea