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Thiourea-catalyzed enantioselective cyanosilylation of ketones.

ABSTRACT: 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.

SUBMITTER: Fuerst DE

PROVIDER: S-EPMC3166885 | biostudies-literature | 2005 Jun

REPOSITORIES: biostudies-literature

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Thiourea-catalyzed enantioselective cyanosilylation of ketones.

Fuerst Douglas E DE Jacobsen Eric N EN

Journal of the American Chemical Society 20050601 25

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. ...[more]

PMID: 15969569

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