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Asymmetric Nucleophilic Catalysis With Planar-Chiral Heterocycles

Three of the most common approaches to accelerating a chemical reaction are to employ Brønsted-acid, Brønsted-base, or Lewis-acid catalysis. A less well-appreciated, but also common, mode of catalysis is nucleophilic (Lewis-base) catalysis. We have developed chiral derivatives of 4-(dimethylamino)pyridine (DMAP), perhaps the most widely used nucleophilic catalyst, that are effective in a diverse array of reactions.

• asymmetric Staudinger synthesis of ß-lactams

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• kinetic resolution of secondary alcohols

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• desymmetrization of meso epoxides

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Selected Publications

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Catalytic Asymmetric Staudinger Reactions to Form ß-Lactams: An Unanticipated Dependence of Diastereoselectivity on the Choice of the Nitrogen Substituent

   

J. Am. Chem. Soc. 2005, 127, 11586-11587.

   

Lee, E. C.; Hodous, B. L.; Bergin, E.; Shih, C.; Fu, G. C.

   

Catalytic Asymmetric Synthesis of Esters from Ketenes

   

J. Am. Chem. Soc. 2005, 127, 6176-6177.

   

Wiskur, S. L.; Fu, G. C.

   

Asymmetric Catalysis with "Planar Chiral" Derivatives of 4-(Dimethylamino)pyridine

   

Acc. Chem. Res. 2004, 37, 542-547.

   

Fu, G. C.

     

Catalytic Enantioselective Synthesis of Quaternary Stereocenters via Intermolecular C-Acylation of Silyl Ketene Acetals: Dual Activation of the Electrophile and the Nucleophile

   

J. Am. Chem. Soc. 2003, 125, 4050-4051.

   

Mermerian, A. H.; Fu, G. C.

     

Enantioselective Addition of Amines to Ketenes Catalyzed by a Planar-Chiral Derivative of PPY: Possible Intervention of Chiral Brønsted-Acid Catalysis

   

J. Am. Chem. Soc. 2002, 124, 10006-10007.

   

Hodous, B. L.; Fu, G. C.

     
     
 
 

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Project Pages: Nucleophilic CatalysisChiral LigandsPalladium and Nickel CatalysisBoron Heterocycles

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Professor Gregory C. Fu
Department of ChemistryMassachusetts Institute of Technology
77 Massachusetts Avenue, Room 18-290
Cambridge, MA 02139-4307 USA

(617) 253-2664 • fax: (617) 258-7500

email: gcf@mit.edu


 

This site was last updated on January 23, 2008

 

 
 

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