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