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Thiourea-Catalyzed Enantioselective Cyanosilylation of Ketones

Douglas E. Fuerst and Eric N. Jacobsen*

*Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02318, Email:

D. E. Fuerst, E. N. Jacobsen, J. Am. Chem. Soc., 2005, 127, 8964-8965.

DOI: 10.1021/ja052511x


A new chiral amino thiourea catalyst 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.

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Key Words

Cyanosilylation, Organocatalysis

ID: J48-Y2005-2420