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Tristan Lambert

Columbia University, Dept. of Chemistry
3000 Broadway
New York, NY 10027

212-854-1438

tl2240@columbia.edu

Lambert Research Group
Selected Publications

Research Summary

From drug design to nanotechnology to materials and beyond, our modern society relies crucially on the ability to prepare complex molecules with atom level control over both connectivity and three-dimensional shape, a capacity enabled by the science of chemical synthesis. The goal of research in the Lambert group is to advance the the field of organic synthesis by inventing transformative new reaction tools that will increase the speed, efficiency, and selectivity with which complex molecules may be constructed.  To accomplish this goal, our efforts are focused on the development of new modes of chemical activation and novel concepts for catalysis.  One of our primary interests has been in the study of aromatic ions, including cyclopropenium ions, tropylium ion, and cyclopentadienyl anions, for the purposes of reaction design and catalysis.  Aromatic ions, those species that satisfy Hückel's rules for aromaticity by the formation of ionic charge, couple the high reactivity of carbon based ions with the accessible stability of aromatics, all within a highly tunable yet readily accessible framework.  As such, they offer tremendous opportunities for the design of advantageous new synthetic methods.   Our group has been pioneering efforts to conceptualize and develop such opportunities.  

 


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Publications

Development of a Catalytic Platform for Nucleophilic Substitution: Cyclopropenone Catalyzed Chlorodehydration of Alcohols.  Vanos, C. M.; Lambert, T. H. Angew. Chem. Int. Ed. 2011, 50, Early View. 

Demonstration of the Facile Reversibility of Fulvene Formation. Bandar, J. S.; Coscia, R. W.; Lambert, T. H. Tetrahedron, 2011, 67, 4364-4370.Special issue in honor of Prof. Dean Toste winning the Tetrahedron Young Investigator Award.

Cyclopropenium Activated Cyclodehydration of Diols.  Kelly, B. D.; Lambert, T. H. Org. Lett., 2011, 13, 740-743.

Tropylium Ion Mediated a-Cyanation of Amines.  Allen, J. M.; Lambert, T. H. J. Am. Chem. Soc., 2011, 133, 1260-1262. 

Cyclopropenium-Activated Beckmann Rearrangement. Catalysis Versus Self-Propagation in Reported Organocatalytic Beckmann Rearrangements. Vanos, C. M.; Lambert, T. H. Chem. Sci., 2010, 1, 705-708.

Aromatic Cation Activation of Carboxylic Acids:  Rapid Generation of Acid Chlorides and Amides. Hardee, D. J.; Kovalchuke, L.; Lambert, T. H. J. Am. Chem. Soc. 2010, 132, 5002-5003.

Aromatic Cation Activation of Alcohols:  Conversion to Alkyl Chlorides Using Dichlorodiphenylcyclopropene. Kelly, B. D.; Lambert, T. H. J. Am. Chem. Soc.2009, 131, 13930-13931. 

Leaving Group Potential of a Substituted Cyclopentadienyl Anion Towards Oxidative Addition. Fisher, E. L; Lambert, T. H. Org. Lett 2009, 11, 4108-4110.  

Demonstration of the Facile Reversibility of Fulvene Formation. Bandar, J. S.; Coscia, R. W.; Lambert, T. H. Tetrahedron, 2011, 67, in press. This article will bepublished as part of a special Symposium-in-Print issue in honor of Prof. Dean Toste winning the Tetrahedron Young Investigator Award.

Cyclopropenium-Activated Cyclodehydration of Diols. Kelly, B. D.; Lambert, T. H. Org. Lett., 2011, 13, 740-743 .

Tropylium Ion Mediated α-Cyanation of Amines. Allen, J. M.; Lambert, T. H. J. Am. Chem. Soc., 2011, 133, 1260-1262.

Cyclopropenium-Activated Beckmann Rearrangement. Catalysis Versus Self-Propagation in Reported Organocatalytic Beckmann Rearrangements. Vanos, C. M.; Lambert, T. H. Chemical Science, 2010, 1, 705-708.

Multicatalysis: Advancing Synthetic Efficiency and Inspiring Discovery. Ambrosini, L. M.; Lambert, T. H. Chem. Cat. Chem. 2010, 2, 1373-1380.

Nucleophilic Acyl Subsitution via Aromatic Cation Activation of Carboxylic Acids: Rapid Generation of Acid Chlorides Under Mild Conditions. Hardee, D. J.; Kovalchuke, L.; Lambert, T. H. J. Am. Chem. Soc. 2010, 132, 5002-5003.

Total Synthesis of the Tylophora Alkaloids Rusplinone, 13aa-Secoantofine, and Antofine using a Multicatalytic Oxidative Aminochlorocarbonylation / Friedel-Crafts Reaction. Ambrosini, L. A.; Cernak, T. A.; Lambert, T. H. Tetrahedron 2010, 66, 4882-4887. This article was published as part of a special Symposium-in-Print issue in honor of Prof. Brian Stoltz winning the Tetrahedron Young Investigator Award.

Development of Oxidative Formylation and Ketonylation Reactions. Ambrosini, L. A.; Cernak, T. A.; Lambert, T. H. Synthesis--Featured Article 2010, 870-881.

Aromatic Cation Activation of Alcohols: Conversion to Alkyl Chlorides Using Dichlorodiphenylcyclopropene. Kelly, B. D.; Lambert, T. H. J. Am. Chem. Soc. 2009, 131, 13930-13931.

Leaving Group Potential of a Substituted Cyclopentadienyl Anion Towards Oxidative Addition. Fisher, E. L; Lambert, T. H. Org. Lett 2009, 11, 4108-4110.

Lanthanum(III) Triflate-Catalyzed Cyclopropanation via Intramolecular Methylene Transfer. Hardee, D. J.; Lambert, T. H. J. Am. Chem. Soc. 2009, 131, 7536-7537.

Multicatalytic Synthesis of Complex Tetrahydrofurans Involving Bismuth(III) Triflate-Catalyzed Intramolecular Hydroalkoxylation of Unactivated Olefins. Kelly, B. D.; Allen, J. M.; Tundel, R. E.; Lambert, T. H. Org. Lett. 2009, 11, 1381-1383.

"Multicatalytic Synthesis of Complex Tetrahydrofurans Involving Bismuth(III) Triflate-Catalyzed Intramolecular Hydroalkoxylation of Unactivated Olefins,"Kelly, B. D.; Allen, J. M.; Tundel, R. E.; Lambert, T. H., Org. Lett. (2009)

"Multicatalytic Synthesis of a-Pyrrolidinyl Ketones via a Tandem Palladium(II)/In(III)-Catalyzed Aminochlorocarbonylation/Friedel-Crafts Acylation Reaction," Cernak, T. A.; Lambert T. H., J. Am. Chem. Soc. (2009)

"Development of a Formal [4+1] Cycloaddition: Pd(OAc)2-Catalyzed Intramolecular Cyclopropanation of 1,3-Dienyl b-Keto Esters and MgI2-Promoted Vinylcyclopropane-Cyclopentene Rearrangement," Coscia, R. W.; Lambert, T. H., J. Am. Chem. Soc. (2009)

"Total Synthesis of UCS1025A," Lambert T. H.; Danishefsky, S. J., J. Am. Chem. Soc.128, 426 (2006)

"Olefin Cross-Metathesis:A Powerful Tool for Constructing Vaccines Composed of Multimeric Antigens,"Wan, Q.; Cho, Y. S.; Lambert, T. H.,J. Carbohydrate Chem. 24, 425 (2005)

"Development of a New Lewis Acid-Catalyzed [3,3]-Sigmatropic Rearrangement:The Allenoate-Claisen Rearrangement," Lambert, T. H.; MacMillan, D. W. C., J. Am. Chem. Soc. 124, 13646 (2002)

 


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