Browsing FAS Scholarly Articles by Author "Jacobsen, Eric"
Now showing items 1-20 of 24
-
Application of a Catalytic Asymmetric Povarov Reaction using Chiral Ureas to the Synthesis of a Tetrahydroquinoline Library
Gerard, Baudouin; O’Shea, Morgan Welzel; Donckele, Etienne; Kesavan, Sarathy; Akella, Lakshmi B.; Xu, Hao; Jacobsen, Eric N.; Marcaurelle, Lisa A. (American Chemical Society, 2012)A 2328-membered library of 2,3,4-trisubstituted tetrahydroquinolines was produced using a combination of solution- and solid-phase synthesis techniques. A tetrahydroquinoline (THQ) scaffold was prepared via an asymmetric ... -
Asymmetric Ion-Pairing Catalysis
Brak, Katrien; Jacobsen, Eric N. (Wiley Blackwell (John Wiley & Sons), 2013) -
Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis
Wasa, Masayuki; Liu, Richard Y.; Roche, Stéphane P.; Jacobsen, Eric N. (American Chemical Society, 2014)We report a scalable, one-pot Mannich route to enantioenriched α-amino esters by direct reaction of α-chloroglycine ester as a practical imino ester surrogate. The reaction is promoted by a chiral aminothiourea, which is ... -
Attractive Noncovalent Interactions in Asymmetric Catalysis: Links Between Enzymes and Small Molecule Catalysts
Knowles, Robert R.; Jacobsen, Eric N. (Proceedings of the National Academy of Sciences, 2010)Catalysis by neutral, organic, small molecules capable of binding and activating substrates solely via noncovalent interactions—particularly H-bonding—has emerged as an important approach in organocatalysis. The mechanisms ... -
Catalytic 1,3-Difunctionalization via Oxidative C–C Bond Activation
Banik, Steven; Mennie, Katrina; Jacobsen, Eric (American Chemical Society (ACS), 2017-06-29)Electronegative substituents arrayed in 1,3-relationships along saturated carbon frameworks can exert strong influence over molecular conformation due to dipole minimization effects. Simple and general methods for incorporation ... -
Chiral Sulfinamide/Achiral Sulfonic Acid Cocatalyzed Enantioselective Protonation of Enol Silanes
Jacobsen, Eric N.; Beck, Elizabeth M.; Hyde, Alan M. (American Chemical Society, 2011)The application of chiral sulfinamides and achiral sulfonic acids as a co-catalyst system for enantioselective protonation reactions is described. Structurally simple, easily accessible sulfinamides were found to induce ... -
Chiral Sulfinamidourea and Strong Brønsted Acid–Cocatalyzed Enantioselective Povarov Reaction to Access Tetrahydroquinolines
Xu, Hao; Zhang, Hu; Jacobsen, Eric N. (Nature Publishing Group, 2014)This protocol describes a method for the laboratory synthesis of enantiomerically enriched, chiral tetrahydroisoquinolines through the application of a chiral sulfinamido urea catalyst for the Povarov reaction. ... -
Chiral Thioureas Promote Enantioselective Pictet–Spengler Cyclization by Stabilizing Every Intermediate and Transition State in the Carboxylic Acid-Catalyzed Reaction
Klausen, Rebekka; Kennedy, C. Rose; Hyde, Alan; Jacobsen, Eric (American Chemical Society (ACS), 2017-08-22)An investigation of the mechanism of benzoic acid/thiourea co-catalysis in the asymmetric Pictet-Spengler reaction is reported. Kinetic, computational, and structure-activity relationship studies provide evidence that ... -
Concerted nucleophilic aromatic substitutions
Kwan, Eugene; Zeng, Yuwen; Besser, Harrison; Jacobsen, Eric (Springer Science and Business Media LLC, 2018-07-16) -
Dual Catalysis in Enantioselective Oxidopyrylium-Based [5+2] Cycloadditions
Burns, Noah; Witten, Michael R; Jacobsen, Eric N. (American Chemical Society, 2011)A new method is reported for effecting catalytic enantioselective intramolecular [5+2] cycloadditions based on oxidopyrylium intermediates. The dual catalyst system consists of a chiral primary aminothiourea and a second ... -
Enantioselective Acylation of Silyl Ketene Acetals through Fluoride Anion-Binding Catalysis
Birrell, James Andrew; Desrosiers, Jean-Nicolas; Jacobsen, Eric N. (American Chemical Society, 2011)A highly-enantioselective acylation of silyl ketene acetals with acyl fluorides has been developed to generate useful \(\alpha\), \(\alpha\)-disubstituted butyrolactone products. This reaction is promoted by a new thiourea ... -
Enantioselective Intramolecular Openings of Oxetanes Catalyzed by (salen)Co(III) Complexes: Access to Enantioenriched Tetrahydrofurans
Loy, Rebecca N.; Jacobsen, Eric N. (American Chemical Society, 2009) -
Enantioselective Selenocyclization via Dynamic Kinetic Resolution of Seleniranium Ions by Hydrogen-Bond Donor Catalysts
Zhang, Hu; Lin, Song; Jacobsen, Eric N. (American Chemical Society, 2014)Highly enantioselective selenocyclization reactions are promoted by the combination of a new chiral squaramide catalyst, a mineral acid, and an achiral Lewis base. Mechanistic studies reveal that the enantioselectivity ... -
Highly Enantioselective, Intermolecular Hydroamination of Allenyl Esters Catalyzed by Bifunctional Phosphinothioureas
Fang, Yuan-Qing; Tadross, Pamela M.; Jacobsen, Eric N. (American Chemical Society, 2014)Bifunctional phosphinothiourea catalysts have been developed successfully for the highly regio- and enantioselective γ-hydroamination of allenyl and propargyl esters with N-methoxy carbamate nucleophiles to yield α,β-unsaturated ... -
Macrocyclic bis-thioureas catalyze stereospecific glycosylation reactions
Park, Yongho; Harper, Kaid; Kuhl, Nadine; Kwan, Eugene; Liu, Richard; Jacobsen, Eric (American Association for the Advancement of Science (AAAS), 2017-01-12)Carbohydrates are involved in nearly all aspects of biochemistry, but their complex chemical structures present long-standing practical challenges to their synthesis. In particular, stereochemical outcomes in glycosylation ... -
Mechanistic Basis for High Reactivity of (salen)Co–OTs in the Hydrolytic Kinetic Resolution of Terminal Epoxides
Nielsen, Lars P. C.; Zuend, Stephan J.; Ford, David Dearborn; Jacobsen, Eric N. (American Chemical Society, 2012)The (salen)Co(III)-catalyzed hydrolytic kinetic resolution (HKR) of terminal epoxides is a bimetallic process with a rate controlled by partitioning between a nucleophilic (salen)Co–OH catalyst and a Lewis acidic (salen)Co–X ... -
Quaternary stereocentres via an enantioconvergent catalytic SN1 reaction
Wendlandt, Alison E.; Vangal, Prithvi; Jacobsen, Eric (Springer Science and Business Media LLC, 2018-04) -
Sensitive and Accurate 13C Kinetic Isotope Effect Measurements Enabled by Polarization Transfer
Kwan, Eugene; Park, Yongho; Besser, Harrison; Anderson, Thayer; Jacobsen, Eric (American Chemical Society (ACS), 2016-12-29)Polarization transfer is demonstrated as a sensitive technique for the measurement of isotopic fractionation of protonated carbons at natural abundance. This method allows kinetic isotope effects (KIEs) to be determined ... -
Structural Analysis of Spiro β-Lactone Proteasome Inhibitors
Groll, Michael; Balskus, Emily Patricia; Jacobsen, Eric N. (American Chemical Society (ACS), 2008)Spiro β-lactone-based proteasome inhibitors were discovered in the context of an asymmetric catalytic total synthesis of the natural product (+)-lactacystin (1). Lactone 4 was found to be a potent inhibitor of the 26S ... -
Synergistic Ion-Binding Catalysis Demonstrated via an Enantioselective, Catalytic [2,3]-Wittig Rearrangement
Kennedy, C. Rose; Guidera, Jennifer A.; Jacobsen, Eric N. (American Chemical Society, 2016)Sigmatropic rearrangements number among the most powerful complexity-building transformations in organic synthesis but have remained largely insensitive to enantioselective catalysis due to the diffuse nature of their ...