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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



• kinetic resolution of secondary alcohols



• desymmetrization of meso epoxides



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



This site was last updated on January 23, 2008



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