CONTACT INFORMATION

Li Deng
Edison-Lecks 322
781-736-2529
deng@brandeis.edu

Li Deng

Deng-2.jpg

Li Deng

Orrie Friedman Distinguished Professor of Chemistry
Ph.D., Harvard University

To fulfill the promises and to meet the challenges of chemistry in the 21st century, chemists must develop new methods to manipulate and create substances of increasing complexity and diversity with dramatically enhanced efficiency and practicality. Our program focuses on the invention and development of new catalytic and selective reactions because of their fundamental importance to molecular science. Our approach involves the discovery and design of accessible catalysts for highly enantioselective asymmetric organic reactions of broad synthetic importance, the elucidation of the reaction mechanism and molecular recognition events underlying the catalytic activity and selectivity, and the applications in the synthesis of chiral compounds of varying complexity.

Our studies following the approach outlined above have led us to the discovery of powerful and practical chiral organic catalysts promoting highly enantioselective reactions by general base catalysis.  We also established that the general base catalysis could be coupled with electrophile-activating catalysis such general acid catalysis and iminium catalysis to form powerful bifunctional catalysis for asymmetric reaction development. These concepts have been successfully applied to the development of a wide range of novel and highly efficient asymmetric reactions of general scopes. Many of these reactions have already found wide applications in target- and diversity-oriented synthesis.  Our reactions have also been developed into viable tools for industrial manufacturing of chiral compounds.

Recent Publications

Lee, J. H.; Deng, L. “Asymmetric approach toward chiral cyclohex-2-enones from anisoles via an enantioselective isomerization by a new chiral diamine catalyst” J. Am. Chem. Soc. 2012, 134, 18209-18212.

Wu Y.; Deng, L. “Asymmetric Synthesis of Trifluoromethylated Amines via Catalytic Enantioselective Isomerization of Imines” J. Am. Chem. Soc. 2012, 134, 14334–14337.

Singh, R.; Deng L. “Cinchona Alkaloid Organocatalysts” in Asymmetric Organocatalysis 2{ Maruoka, K., Ed. Science of Synthesis, Georg Thieme Verlag KG: Stuttgart. New York, 2012, Chapter 2.1.2, 41-117.

Provencher, B.; Bartelson, K.; Liu, Y.; Deng, L. “Structural Study-Guided Development of Versatile Phase-Transfer Catalysts for Asymmetric Conjugate Additions of Cyanide” Angew. Chem. Int. Ed.  2011, 50, 10565-10569. (Designated as a “Hot Paper”).

Wu, Y.; Singh, R.; Deng, L. “Asymmetric Olefin Isomerization via Proton Transfer Catalysis with an Organic Molecule” J. Am. Chem. Soc. 2011, 133, 12458-12461.

Campbell, N.; Sun, B.; Deng, L. “Cinchona alkaloid-catalyzed enantioselective amination of α,β-unsaturated ketones: an asymmetric approach to 2-pyrazoline” Advanced Synthetsis&Catalysis 2011, 353, 3123-3128..

Bartelson, K.; Singh, R.; Foxman, B. F.; Deng, L. “Catalytic Asymmetric [4+2] Additions with Aliphatic Nitroalkenes” Chemical Sciences 2011, 2, 1940-1944.

Liu, Y.; Provencher, B.; Bartelson, K.; Deng, L. “Asymmetric Darzens Reaction with a Bifunctional Phase Transfer Catalyst” Chemical Sciences 2011, 2, 1301-1304.

Li, H.; Chen, Y. G.; Deng, L. “Cinchona Alkaloids” in Privileged Catalysts and Ligands in Asymmetric Catalysis" Zhou, Q.-L., Ed.; Wiley-VCH Verlag&Co. KGaA.: Boschstr, Weinheim, Germany,  2011, Chapter 10, 361-404.

“Asymmetric Vinylogous Aldol Reactions of Silyloxy Furans with a Chiral Organic Salt”  Singh, R. P.; Foxman, B. F.; Deng L. J. Am. Chem. Soc. 2010, 132, 9558-9560.  
 
“Elucidation of the Active Conformation of Cinchona Alkaloid Catalyst and Chemical Mechanism of Alcoholysis of Meso Anhydrides,” Li, H.; Liu, X.; Wu, F.; Tang, L.; Deng, L. PNAS, 2010, Published online before print June 21, 2010, doi: 10.1073/pnas.1004439107.

“Cinchona alkaloid catalyzed asymmetric amination of α,β-unsaturated ketones: a novel asymmetric approach to 2-pyrazolines” Campbell, N. R.; Sun, B.; Deng L.  2010, submitted.

Wang, Y.; Deng, L. “Asymmetric Acid-Base Bifunctional Catalysis with Organic Molecules” in CatalyticAsymmetric Synthesis,” Ojima, I., Ed.; John Wiley & Sons Inc.: Hoboken, New Jersey 2010, Chapter 2.2B. 59-94.

“Asymmetric Total Synthesis of (-)-Plicatic Acid via a Highly Enantioselective and Diastereoselective Nucleophilic Epoxidation of Acyclic Trisubstituted Olefins,” Sun, B.; Hong, R.; Kang, Y.-B.  J. Am. Chem. Soc. 2009, 131, 10384-10385.

 

“Catalytic Asymmetric Amination of a-Substituted b-Keto Thioesters,” Liu, X.;    Sun, B.; Deng, L. Synlett, 2009, 1685-1689 (invited contribution for a cluster   issue of bifunctional catalysis).

“Asymmetric Synthesis of β,γ-Unsaturated α-Amino Acids via Cinchona Alkaloid-Catalyzed Kinetic Resolution of Urethane-Protected α-Amino Acid N- Carboxyanhydrides (UNCAs),” Hang, J.; Deng, L. Bioorganic and Medicinal Chemistry Letters, 2009, 19, 3856-3858 (invited contribution to Barbas SIP).

“Catalytic Asymmetric Conjugate Addition of Simple Alkyl Thiols to a,b- Unsaturated N-Acylated Oxazolidin2-ones with Bifunctional Catalysts,” Liu, Y.; Sun, B.; Wang, B.; Matthew, W.; Deng L. J. Am. Chem. Soc.2009, 131, 418-419.

“Synthesis of Application of Chiral a-Amino Acids by Kinetic Resolution of Urethane-Protected a-Amino Acid N-Carboxyanhydrides with Modified   Cinchona Alkaloid Catalysts,” Hang, J.; Ishii, Y.; Furukawa, Y.; Deng, L., Soloshonok, V. A.; Izawa, K. Ed., ACS Symposium Series 1009, American Chemical Society: Washington, DC 2009; 265-287.

Wang, Y.; Deng, L. “Asymmetric Acid-Base Bifunctional Catalysis with Organic Molecules,” in Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 2009, Chapter 2.2. in press.

Catalytic Enantioselective Conjugate Additions with a,b-Unsaturated Sulfones,”Li, H.; Song, J.; Deng, L. Tetrahedron, 2009, 65, 3139-3148. (invited contribution to DuBois TSIP).

“Asymmetric Aza-Michael Reactions of a,b-Unsaturated Ketones with Bifunctional Organic Catalysts,” Lu X.; Deng, L.  Angew. Chem. Int. Ed.  2008, 7710-7713.

“Catalytic Enantioselective Peroxidation of a,b-Unsaturated Ketones,” Lu, X.; Liu, Y.; Sun, B.; Cindric, B.; Deng, L. J. Am. Chem. Soc. 2008, 130, 8134-8135.

“Enantioselective Diels-Alder Reactions of Simple a,b-Unsaturated Ketones with a Cinchona Alkaloid Catalyst,” Singh, R. P.; Bartelson, K., Wang, Y.; Su, H.; Lu, X.; Deng, L. J. Am. Chem. Soc.2008, 130, 2422-2423.

“Asymmetric Diels-Alder Reactions of 2-Pyrones with Bifunctional Organic Catalysts,” Wang, Y.; Li, H.; Wang, Y.-Q.; Liu, Y.; Foxman, B. M.; Deng, L. J. Am. Chem. Soc. 2007,129, 6364-6365.

“An Approach to Skeletal Diversity Using Functional Group Pairing of Multifunctional Scaffolds” Comer E.; Deng, L.; Proco,  J. A. Jr. Organic Lett. 2007, 9, 2123-2126.

“Asymmetric Mannich Reactions with in situ Generation of Carbamate-Protected Imines by an Organic Catalyst,” Song, J.; Shih, H.; Deng, L.Organic Lett.2007, 9, 603-606.

“Control of Diastereoselectivity in Tandem Asymmetric Reactions Generating Nonadjacent Stereocenters with Bifunctional Catalysis by Cinchona Alkaloids,” Wang, B.; Wu, F.; Wang, Y.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2007,129, 768‑769.

"Enantioselective Friedel-Crafts Reaction of Indoles with Carbonyls Catalyzed by Bifunctional Cinchona Alkaloids," Li, H.; Wang, Y.: Deng, L. Organic Lett. 2006, 8, 4063-4065.

"Enantioselective Cyanocarbonation of Ketones with Chiral Base,"  Tian, S.-K.; Deng, L. Tetrahedron, 2006, 62, 11320-11330 (invited contribution to MacMillan TSIP).

“Asymmetric Friedel-Crafts Reaction of Indoles with Imines by an Organic Catalyst,” Wang, Y.; Song, J.; Hong R.; Li, H.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156-8157.

"Asymmetric Synthesis of Chiral Aldehydes via Conjugate Additions with Bifunctional Organocatalysis by Cinchona Alkaloids,” Wu, F.-H.; Ran, H.; Khan, J.; Deng, L. Angew. Chem. Int. Ed.  2006, 45, 4301-4305. (Designated as a “Hot Paper”).

“The Mannich Reaction of Malonates with Simple Imines Catalyzed by Bifunctional Cinchona Alkaloids:  Enantioselective Synthesis of b‑Amino Acids,” Song, J.; Wang, Y.; Deng, L. J. Am. Chem. Soc. 2006, 128,6048-6049.

“Dual-Function Cinchona Alkaloid Catalysis: Catalytic Asymmetric Tandem Conjugate Addition-Protonation for the Direct Creation of Nonadjacent Stereocenters,” Wang, Y.; Liu, X.; Deng, L. J. Am. Chem. Soc. 2006, 128, 3928‑3930.

“Enantioselective Nitroaldol Reaction of a-Ketoesters Catalyzed by Cinchona Alkaloids,” Li, H.; Wang, B.; Deng, L.  J. Am. Chem. Soc. 2006, 128, 732-733.    

Construction of Quaternary Stereocenters via Efficient and Practical Conjugate Additions to α,β‑Unsaturated Ketones with a Chiral Organic Catalyst,” Wu, F.-H.; Li, H.; Hong, R.; Deng, L. Angew. Chem. Int. Ed.  2006, 45, 947-950.

“Catalytic Enantioselective Conjugate Additions with Vinyl Sulfones,” Li, H.; Song, J.; Liu, X.; Deng, L.  J. Am. Chem. Soc. 2005, 127, 8948-8949.

"Catalytic Enantioselective Total Syntheses of Bisorbicillinolide, Bisorbicillinol and Bisorbibutenolide," Hong, R.; Chen, Y.; Deng, L. Angew. Chem. Int. Ed. 2005, 44, 3478-3481.

“Catalytic Construction of Nitrogen-Substituted Quaternary Stereocenter by Highly Enantioselective Amination with Chiral Catalyst Derived from Both Quinine and Quinidine,” Liu, X.; Li, H.; Deng, L. Organic Lett. 2005, 8, 167-169.

“Stereocontrolled Creation of Adjacent Quaternary and Tertiary Stereocenters via a Catalytic, Diastereoselective and Enantioselective Conjugate Addition,” Li, H.; Wang, Y.; Tang, L.; Wu, F.;  Liu, X.; Guo, C.; Foxman, B.; Deng, L. Angew. Chem. Int. Ed. 2005, 44, 105-108 (designated as a “Very Important Paper (VIP)” paper).

Highly Enantioselective Conjugate Addition of Malonate and b-Ketoester to Nitroalkenes: Asymmetric C-C Bond Formation via New Bifunctional Organic Catalysts Based on Cinchona Alkaloids,” Li, H.; Wang, Y.; Tang, L.; Deng, L.  J. Am. Chem. Soc. 2004, 126, 9906-9907.

“Asymmetric Organic Catalysis with Modified Cinchona Alkaloids,” Tian, S.-K.; Chen, Y.; Hang, Jianfeng.; Tang, Liang.; McDaid, P.; Deng, L. Accounts of Chemical Research 2004, 37, 621-631 (invited contribution for a special issue of asymmetric organic catalysis).

“Dynamic Kinetic Resolution for Asymmetric Synthesis of a-Alkyl Amino Acids via Dual-Function Catalysis of Modified Cinchona Alkaloids,” Hang, J.; Deng, L. Synlett, 2003, 1927-1930 (invited paper for cluster papers of organic catalysis).

“Asymmetric Alcoholysis of Cyclic Anhydrides,” Chen, Y.; McDaid, P.; Deng, L. Chem. Review 2003, 103, 2965-2984 (invited review article for a thematic issue of Enantioselective Catalysis).

“Catalytic Asymmetric Cyanosilylation of Ketones with Chiral Lewis Base,” Tian, S.-K.; Hong, R.; Deng, L.  J. Am. Chem. Soc. 2003, 125, 9900-9901.

“Development of a Rapid, Room Temperature Dynamic Kinetic Resolution for Efficient Asymmetric Synthesis of a-Aryl Amino Acids,” Hang, J.; Li, H.; Deng, L. Organic Lett. 2002, 4, 3321-3324.

“Dynamic Kinetic Resolution via Dual-Function Catalysis of Modified Cinchona Alkaloids: Asymmetric Synthesis of a-Hydroxy Carboxylic Acids,” Tang, L.; Deng, L. J. Am. Chem. Soc. 2002, 124, 2870-2871.

“A Highly Enantioselective and General Conjugate Addition of Thiols to Cyclic Enones with an Organic Catalyst,” McDaid, P.; Chen, Y.; Deng, L.  Angew. Chem. Int. Ed. 2002, 41, 338-340. Angew. Chem. 2002, 114, 348-350. (Designated as a “Hot Paper”). 

“Asymmetric Synthesis of a-Amino Acids via Cinchona Alkaloid-Catalyzed Kinetic Resolution of Urethane-Protected a-Amino Acid N-Carboxyanhydrides (UNCA),” Hang, J.; Tian, S.-K.; Tang, L.; Deng, L. J. Am. Chem. Soc. 2001,123, 12696-12697.

“Parallel Kinetic Resolutions of Monosubstituted Succinic Anhydrides Catalyzed by a Modified Cinchona Alkaloid,” Chen, Y.; Deng, L. J. Am Chem. Soc. 2001, 123, 11302-11303.

“A Formal Catalytic Asymmetric Synthesis of (+)-Biotin with Modified Cinchona Alkaloids,” Choi, C.; Tian, S.-K.; Deng, L. Synthesis, 2001, 1737-1741 (invited contribution for a special issue of organic catalysis).

"A Highly Enantioselective Chiral Lewis Base-Catalyzed Asymmetric Cyanation of Ketones,"Tian, S.-K.; Deng, L.  J. Am. Chem. Soc. 2001, 123, 6195-6196.

"A Highly Enantioselective Catalytic Desymmetrization of Cyclic Anhydrides with Modified Cinchona Alkaloids," Chen, Y.; Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2000, 122, 9542-9543.