个人简介

Eric Jacobsen joined Harvard University as full professor in 1993, was named the Sheldon Emory Professor of Organic Chemistry in 2001, and served as Chair of the Department of Chemistry and Chemical Biology between 2010 and 2015. He directs a research group of 20 graduate students and postdocs dedicated to discovering useful catalytic reactions, and to applying state-of-the art mechanistic and computational techniques to the analysis of those reactions. Several of the catalysts developed in his labs have found widespread application in industry and academia. These include metal-salen complexes for asymmetric epoxidation, conjugate additions, and hydrolytic kinetic resolution of epoxides; chromium-Schiff base complexes for a wide range of enantioselective pericyclic reactions; and organic hydrogen bond-donor catalysts for activation of neutral and cationic electrophiles. Eric's mechanistic analyses of these systems have helped uncover general principles for catalyst design, including electronic tuning of selectivity, cooperative homo- and hetero-bimetallic catalysis, hydrogen-bond donor asymmetric catalysis, and anion binding catalysis.

研究领域

Catalyst Discovery Mechanism Synthetic Applications Reaction Gallery

Our program is dedicated to the discovery of practical catalytic reactions, and to the application of state-of-the art mechanistic and computational techniques to the analysis of those reactions. Over the past several years, we have sought and identified new classes of chiral catalysts, and several of these have found widespread application in industry and academia. These include metal-salen complexes for asymmetric epoxidation, conjugate additions, and hydrolytic kinetic resolution of epoxides; copper-diimine complexes for asymmetric aziridination; chromium-Schiff base complexes for a wide range of enantioselective pericyclic reactions; and organic hydrogen bond-donor catalysts for activation of neutral and cationic electrophiles. Our mechanistic analyses of these catalytic systems have helped uncover general principles for future catalyst design, including electronic tuning of enantioselectivity, cooperative homo- and hetero-bimetallic catalysis, hydrogen-bond donor asymmetric catalysis, and anion binding catalysis. While the identification of useful catalysts represents an immediate goal of our work, the broader objective is to help lay the foundation for the rational design of functional molecules. Despite the organic chemists’ advanced understanding of structure, bonding, and reactivity principles, the discovery and optimization of functional molecules of any type (catalysts, medicines, materials) remains a largely empirical endeavor. With the goal of identifying general design principles, we apply the most rigorous methods of physical-organic chemistry to elucidate the mechanism of action of effective catalysts, with an emphasis on learning about the attractive and destabilizing interactions in transition structures. We think this will lead to insights into how to devise either improved catalysts for known reactions, or brand-new classes of catalysts for novel applications. And, in the long term, we hope this knowledge will allow scientists to approach the highly ambitious and important goal of rational design of both novel catalysts and other functional small molecules.

近期论文

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“Andreas Pfaltz, Inspiration and Friend,” Jacobsen, E.N.; Adv. Synth. Catal. 2022, 364, 3324. “Evidence for Oxonium Ions in Ethereal ‘Hydrogen Chloride’,” Wagen, C. C.; Jacobsen, E.N.; Organic Lett. 2022, 24, 8826-8831. “Exploring Structure–Function Relationships of Aryl Pyrrolidine-Based Hydrogen-Bond Donors in Asymmetric Catalysis using Data-Driven Techniques,” Mohammad, S.; Hofstra Wahlman, J.; Read, J.; Werth, J.; Jacobsen, E.N.; Sigman, M. S.; ACS Catal. 2022, 12, 14836–14845. “Screening for Generality in Asymmetric Catalysis,” Wagen, C. C.; McMinn, S. E.; Kwan, E. E.; Jacobsen, E.N.; Nature 2022, 610, 680-686. “Chloride-Mediated Alkene Activation Drives Enantioselective Thiourea and Hydrogen Chloride Co-Catalyzed Prins Cyclizations,” Kutateladze, D. A.; Wagen, C. C.; Jacobsen, E.N.; J. Am. Chem. Soc. 2022, 144, 15812-15824. “Site-Selective, Stereocontrolled Glycosylation Catalyzed by Bis-Thioureas,” Li, Q.; Levi, S. M.; Wagen, C. C.; Wendlandt, A. E; Jacobsen, E.N.; Nature 2022, 608, 74-79. “Enantioselective hydrogen-bond-donor catalysis to access diverse stereogenic-at-P(V) compounds,” Forbes, K.A.; Jacobsen, E.N.; Science 2022, 376, 1230-1236. “Catalytic Alkene Difunctionalization Reactions,”Ovian, J.M.; Jacobsen, E.N.; in Iodine Catalysis in Organic Synthesis Ishihara, K., Muniz, K., Eds; Wiley-VCH GmbH: Weinheim, Ch.9, 243-274. “Chiral Ureas, Thioureas, and Squaramides in Anion-Binding Catalysis with Co-catalytic Bronsted/Lewis Acids,” Trotta, A.; Jacobsen, E.N.; in Anion Binding Catalysis Garcia Mancheno, O., Eds.;Wiley-VCH GmbH: Weinheim, Ch.4, 9585-9594. “Cooperative Hydrogen-Bond-Donor Catalysis with Hydrogen Chloride Enables Highly Enantioselective Prins Cyclization Reactions,” Kutateladze, D.A.; Jacobsen, E.N.; J. Am. Chem. Soc. 2021, 143, 20077-20083. “Enantioselective catalystic 1,2-boronate rearrangements,” Sharma, H.A.; Essman, J.Z.; Jacobsen, E.N.; Science 2021, 374, 752-757. “A Case Study in Catalyst Generality: Simultaneous Highly-Enantioselective Bronsted- and Lewis-Acid Mechanisms in Hydrogen-Bond-Donor Catalyzed Oxetane Openings,” Strassfeld, D.A.; Algera, R.F.; Wickens, Z.K.; Jacobsen, E.N.; J. Am. Chem. Soc. 2021, 143, 9585-9594. “Enantioselective, Catalytic Multicomponent Synthesis of Homoallylic Amines Enabled by Hydrogen-Bonding and Dispersive Interactions,” Ronchi, E.; Paradine, S.M.; Jacobsen, E.N.; J. Am. Chem. Soc. 2021, 143, 7272-7278. “The Aryl-Pyrrolidine-tert-Leucine Motif as a New Privileged Chiral Scaffold: The Role of Non-Covalent Stabilizing Interactions,” Strassfeld, D.A.; Jacobsen, E.N., in Supramolecular Catalysis: New Directions and Developments, van Leeuwen, Raynal, Eds.; Wiley, New York, ISBN 978-3-527-34902-9, Chapter 25. “Enantioselective Aryl-Iodide-Catalyzed Wagner–Meerwein Rearrangements,”Sharma, H.A.; Mennie, K.M.; Kwan, E.E.; Jacobsen, E.N.; J. Am. Chem. Soc. 2020, 142, 16090-16096. “Catalytic Enantioselective Synthesis of Difluorinated Alkyl Bromides,”Levin, M.D.; Ovian, J.M.; Read, J.A.; Sigman, M.S.; Jacobsen, E.N.; J. Am. Chem. Soc. 2020, 142, 14831–14837. “Asymmetric Nazarov Cyclizations of Unactivated Dienones by Hydrogen-Bond-Donor/Lewis Acid Co-Catalyzed, Enantioselective Proton-Transfer,” Metternich, J.; Reiterer, M.; Jacobsen, E.N.; Adv. Synth. Catal. 2020, 362, 4092-4097. “Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea,” Li, Q.; Levi, S.M.; Jacobsen, E.N.; J. Am. Chem. Soc. 2020, 142, 11865-11872. “Highly Enantioselective, Hydrogen-Bond-Donor Catalyzed Additions to Oxetanes,” Strassfeld, D.A.; Wickens, Z.K.; Picazo, E.; Jacobsen, E.N.; J. Am. Chem. Soc. 2020, 142, 9175-9180. “Enantioselective Tail-to-Head Cyclizations Catalyzed by Dual-Hydrogen-Bond Donors,” Kutateladze, D.A, Strassfeld, D.A.; Jacobsen, E.N.; J. Am. Chem. Soc. 2020, 142, 6951-6956.