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Communication

Thiourea-Catalyzed Enantioselective Cyanosilylation of Ketones

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Douglas E. Fuerst and Eric N. Jacobsen*

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

J. Am. Chem. Soc., 2005, 127 (25), pp 8964–8965

DOI: 10.1021/ja052511x

Publication Date (Web): June 4, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jacobsen@chemistry.harvard.edu

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.

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Published In Issue June 29, 2005
Received April 18, 2005

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Communication

Thiourea-Catalyzed Enantioselective Cyanosilylation of Ketones

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Cooperative Catalysis by Tertiary Amino-Thioureas: Mechanism and Basis for Enantioselectivity of Ketone Cyanosilylation

Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts

Asymmetric Catalytic Mannich Reactions Catalyzed by Urea Derivatives: Enantioselective Synthesis of β-Aryl-β-Amino Acids

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