The Lectka Group at Johns Hopkins University

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Selected Publications

• DeBlase, A. F.; Scerba, M. T.; Lectka, T.; Johnson, M. A.  "Vibrational predissociation spectroscopy of Ar-tagged, trisubstituted silyl cations" Chem. Phys. Lett. 2013, in press PDF
• Struble, M. D.; Scerba, M. T.; Siegler, M.; Lectka, T.  "Evidence for a Symmetrical Fluoronium Ion in Solution" Science 2013, 340, 57-60 PDF
• Bloom, S.; Pitts, C. R.; Woltornist, R.; Griswold, A.; Holl, M. G.; Lectka, T.  "Iron(II)-Catalyzed Benzylic Fluorination" Org. Lett. 2013, 15, 1722-1724 PDF
• Bloom, S.; Pitts, C. R.; Miller, D.; Haselton, N.; Holl, M. G.; Urheim, E.; Lectka, T.  "A Polycomponent Metal-Catalyzed Aliphatic, Allylic, and Benzylic Fluorination" Angew. Chem. Int. Ed. Engl. 2012, 51, 10580-10583 PDF
• Erb, J.; Strull, J.; Miller, D.; He, J.; Lectka, T.  "The Diels–Alder Cyclization of Ketenimines" Org. Lett. 2012, 14(8), 2191-2193 PDF
• Scerba, M. T.; DeBlase, A. F.; Bloom, S.; Dudding, T.; Johnson, M. A.; Lectka, T.  "Characterization of Highly Unusual NH⁺–O Hydrogen Bonding to Ester Ether Oxygen Atoms through Spectroscopic and Computational Studies" J. Phys. Chem. 2012, 116(14), 3556-3560 PDF
• Scerba, M. T.; Bloom, S.; Haselton, N.; Siegler, M.; Jaffe, J.; Lectka, T.  "Interaction of a C-F Bond with the pi-System of a C=C Bond or 'Head On' with a Proximate C-H Bond." J. Org. Chem. 2012, 77, 1605-1609 PDF
• Scerba, M. T.; Leavitt, C. M.; Diener, M. E.; Deblase, A. F.; Guasco, T. L.; Siegler, M. A.; Bair, N.; Johnson, M. A.; Lectka, T.  "NH⁺-F Hydrogen Bonding in a Fluorinated "Proton Sponge" Derivative: Integration of Solution, Solid-State, Gas-Phase, and Computational Studies" J. Org. Chem. 2011, 76, 7975-7984 PDF
• Bloom, S.; Scerba, M. T.; Erb, J.; Lectka, T.  "Tricomponent Catalytic alpha,alpha-difluorination of Acid Chlorides" Org. Lett. 2011, 13, 5068-5071 PDF
• Erb, J.; Paull, D. H.; Belding, L.; Dudding, T.; Lectka, T.  "From Bifunctional to Trifunctional (Tricomponent Nucleophile–Transition Metal–Lewis Acid) Catalysis: The Catalytic, Enantioselective alpha-Fluorination of Acid Chlorides" J. Am. Chem. Soc. 2011, 133, 7536-7546 PDF
• Erb, J.; Alden-Danforth, E.; Kopf, N.; Scerba, M. T.; Lectka, T.  "Combining Asymmetric Catalysis with Natural Product Functionalization through Enantioselective alpha-Fluorination" J. Org. Chem. 2010, 75(3), 969-971 PDF
• Paull, D. H.; Weatherwax, A.; Lectka, T.  "Catalytic, Asymmetric Reactions of Ketenes and Ketene Enolates" Tetrahedron 2009, 65(34), 6771-6803 PDF
• Abraham, C.; Paull, D. H.; Dogo-Isonagie, C.; Lectka, T.  "Diastereoselective Synthesis of trans-beta-Lactams Using a Simple Multifunctional Catalyst" Synlett 2009, 10, 1651-1654 PDF
• Paull, D. H.; Scerba, M. T.; Alden-Danforth, E.; Widger, L. R.;  Lectka, T.  "Catalytic, Asymmetric alpha-Fluorination of Acid Chlorides: Dual Metal-Ketene Enolate Activation" J. Am. Chem. Soc. 2008, 130(51), 17260-17261 PDF
• Abraham, C. J.; Paull, D. H.; Bekele, T.; Scerba, M. T.; Dudding, T; Lectka, T. "A Surprising Mechanistic 'Switch' in Lewis Acid Activation: A Bifunctional, Asymmetric Approach to alpha-Hydroxy Acid Derivatives" J. Am. Chem. Soc. 2008, 130(50), 17085-17094 PDF
• Alden-Danforth, E.; Scerba, M. T.; Lectka, T. "Asymmetric Cycloadditions of o-Quinone Methides Employing Chiral Ammonium Fluoride Precatalysts" Org. Lett. 2008, 10(21), 4951-4953 PDF
• Singh, P.; Williams, S. A.; Shah, M. H.; Lectka, T.; Pritchard, G. J.; Isaacs, J. T.; Denmeade, S. R. "Mechanistic Insights into the Inhibition of Prostate Specific Antigen by beta-Lactam Class Compounds" Proteins-Structure Function and Bioinformatics 2008, 70(4), 1416-1428 PDF
• Paull, D. H.; Abraham, C. J.; Scerba, M. T.; Alden-Danforth, E.; Lectka, T. "Bifunctional Asymmetric Catalysis: Cooperative Lewis Acid/Base Systems" Acc. Chem. Res. 2008, 41(5), 655-663 PDF
• Paull, D. H.; Wolfer, J.; Grebinski, J. W.; Weatherwax, A.; Lectka, T. "Catalytic, Asymmetric Inverse Electron Demand Hetero Diels-Alder Reactions of o-Benzoquinone Derivatives and Ketene Enolates" Chimia 2007, 61(5), 240-246 PDF
• Paull, D. H.; Alden-Danforth, E.; Wolfer, J.; Dogo-Isonagie, C.; Abraham, C. J.; Lectka, T. "An Asymmetric, Bifunctional Catalytic Approach to Non-Natural alpha-Amino Acid Derivatives" J. Org. Chem. 2007, 72(14), 5380-5382 PDF
• Dogo-Isonagie, C.; Bekele, T.; France, S.; Wolfer, J.; Weatherwax, A.; Taggi, A. E.; Paull, D. H.; Dudding, T.; Lectka, T. "A Mechanistic Study on the Catalytic, Asymmetric alpha-Bromination of Acid Chlorides" Eur. J. Org. Chem. 2007, 1091-1100 PDF
• Dogo-Isonagie, C.; Bekele, T.; France, S.; Wolfer, J.; Weatherwax, A.; Taggi, A. E.; Lectka, T. "Scalable Methodology for the Catalytic, Asymmetric alpha-Bromination of Acid Chlorides" J. Org. Chem. 2006, 71(23), 8946-8949 PDF
• Abraham, C. J.; Paull, D. H.; Scerba, M. T.; Grebinski, J. W.; Lectka, T. "Catalytic, Enantioselective Bifunctional Inverse Electron Demand Hetero-Diels--Alder Reactions of Ketene Enolates and o-Benzoquinone Diimides" J. Am. Chem. Soc. 2006, 128(41), 13370-13371 PDF
• Wolfer, J.; Bekele, T.; Abraham, C. J.; Dogo-Isonagie, C.; Lectka, T. "Catalytic, Asymmetric Synthesis of 1,4-Benzoxazinones: A Remarkably Enantioselective Route to alpha-Amino Acid Derivatives from o-Benzoquinone Imides" Angew. Chem. Int. Ed. 2006, 45(44), 7398-7400 PDF
• Bekele, T.; Shah, M. H.; Wolfer, J.; Abraham, C. J.; Weatherwax, A.; Lectka, T. "Catalytic, Enantioselective [4 + 2]-Cycloadditions of Ketene Enolates and o-Quinones: Efficient Entry to Chiral, alpha-Oxygenated Carboxylic Acid Derivatives" J. Am. Chem. Soc. 2006, 128(6), 1810-1811 PDF
• Weatherwax, A.; Abraham, C. J.; Lectka, T. "An Anionic Nucleophilic Catalyst System for the Diastereoselective Synthesis of trans-beta-Lactams" Org. Lett. 2005, 7(16), 3461-3463 PDF
• France, S.; Bernstein, D.; Weatherwax, A.; Lectka, T. "Performing the Synthesis of a Complex Molecule on Sequentially Linked Columns: Toward the Development of a 'Synthesis Machine'" Org. Lett. 2005, 7(14), 3009-3012 PDF
• France, S.; Weatherwax, A.; Lectka, T. "Recent Developments in Catalytic, Asymmetric alpha-Halogenation: A New Frontier in Asymmetric Catalysis" Eur. J. Org. Chem. 2005, 475-479 PDF
• France, S.; Shah, M.; Weatherwax, A.; Wack, H.; Roth, J.; Lectka, T. "Bifunctional Lewis Acid-Nucleophile-Based Asymmetric Catalysis: Mechanistic Evidence for Imine Activation Working in Tandem with Chiral Enolate Formation in the Synthesis of beta-Lactams" J. Am. Chem. Soc. 2005, 127(4), 1206-1215 PDF
• Bernstein, D.; France, S.; Wolfer, J.; Lectka, T. “A column based 'flush and flow' system for the asymmetric alpha-chlorination of acid halides” Tetrahedron: Asymmetry 2005, 16, 3481-3483 PDF
• France, S.; Weatherwax, A.; Taggi, A. E.; Lectka, T. “Advances in the Catalytic, Asymmetric Synthesis of beta-Lactams” Acc. Chem. Res. 2004, 37(8), 592-600 PDF
• Wack, H.; France, S.; Hafez, A. M.; Drury, W. J., III; Weatherwax, A.; Lectka, T. “Development of a New Dimeric Cyclophane Ligand: Application to Enhanced Diastereo- and Enantioselectivity in the Catalytic Synthesis of beta-Lactams” J. Org. Chem. 2004, 69(13), 4531-4533 PDF
• France, S.; Wack, H.; Taggi, A. E.; Hafez, A. M.; Wagerle, T. R.; Shah, M. H.; Dusich, C. L.; Lectka, T. “Catalytic, Asymmetric alpha-Chlorination of Acid Halides” J. Am. Chem. Soc. 2004, 126(13), 4245-4255 PDF
• Shah, M. H.; France, S.; Lectka, T. “Bicarbonate Salts as Cost-Effective Bases for the Synthesis of Ketenes and Their Synthetic Equivalents Applied to the Asymmetric Synthesis of beta-Lactams” Synlett 2003, 12, 1937-1939 PDF
• France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. “Nucleophilic Chiral Amines as Catalysts in Asymmetric Synthesis” Chem. Rev. 2003, 103(8), 2985-3012 PDF
• Hafez, A. M.; Dudding, T.; Wagerle, T. R.; Shah, M. H.; Taggi, A. E.; Lectka, T. “A Multistage, One-Pot Procedure Mediated by a Single Catalyst: A New Approach to the Catalytic Asymmetric Synthesis of alpha-Amino Acids” J. Org. Chem. 2003, 68(15), 5819-5825 PDF
• Taggi, A. E.; Hafez, A. M.; Lectka, T. “alpha-Imino Esters: Versatile Substrates for the Catalytic, Asymmetric Synthesis of alpha- and beta-Amino Acids and beta-Lactams” Acc. Chem. Res. 2003, 36(1), 10-19 PDF
• Hafez, A. M.; Taggi, A. E.; Lectka, T. “Sequential Column Asymmetric Catalysis” Chem.—Eur. J. 2002, 8(18), 4114-4119 PDF
• Taggi, A. E.; Hafez, A. M.; Dudding, T.; Lectka, T. “Molecular Mechanics Calculations as Predictors of Enantioselectivity for Chiral Nucleophile Catalyzed Reactions” Tetrahedron 2002, 58(41), 8351-8356. PDF
• Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Ferraris, D.; Lectka, T. “The Development of the First Catalyzed Reaction of Ketenes and Imines: Catalytic, Asymmetric Synthesis of beta-Lactams” J. Am. Chem. Soc. 2002, 124(23), 6626-6635 PDF
• France, S.; Wack, H.; Hafez, A. M.; Taggi, A. E.; Witsil, D. R.; Lectka, T. “Bifunctional Asymmetric Catalysis: A Tandem Nucleophile/Lewis Acid Promoted Synthesis of beta-Lactams” Org. Lett. 2002, 4(9), 1603-1605 PDF
• Taggi, A. E.; Wack, H.; Hafez, A. M.; France, S.; Lectka, T. “Generation of Ketenes from Acid Chlorides Using NaH/Crown Ether Shuttle-Deprotonation for Use in Asymmetric Catalysis” Org. Lett. 2002, 4(4), 627-629 PDF
• Dudding, T.; Hafez, A. M.; Taggi, A. E.; Wagerle, T. R.; Lectka, T. "A Catalyst that Plays Multiple Roles: Asymmetric Synthesis of beta-Substituted Aspartic Acid Derivatives through a Four-Stage, One-Pot Procedure” Org. Lett. 2002, 4(3), 387-390 PDF
• Ferraris, D.; Young, B.; Cox, C.; Dudding, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. “Catalytic, Enantioselective Alkylation of alpha-Imino Esters: The Synthesis of Nonnatural alpha-Amino Acid Derivatives” J. Am. Chem. Soc. 2002, 124(1), 67-77 PDF
• Hafez, A. M.; Taggi, A. E.; Dudding, T.; Lectka, T. “Asymmetric Catalysis on Sequentially-Linked Columns” J. Am. Chem. Soc. 2001, 123(44), 10853-10859 PDF
• Hafez, A. M.; Taggi, A. E.; Wack, H.; Esterbrook, J.; Lectka, T. “Reactive Ketenes through a Carbonate/Amine Shuttle Deprotonation Strategy: Catalytic, Enantioselective alpha-Bromination of Acid Chlorides” Org. Lett. 2001, 3(13), 2049-2051 PDF
• Wack, H.; Taggi, A. E.; Hafez, A. M.; Drury, W. J., III; Lectka, T. “Catalytic, Asymmetric alpha-Halogenation” J. Am. Chem. Soc. 2001, 123(7), 1531-1532 PDF
• Hafez, A. M.; Taggi, A. E.; Wack, H.; Drury, W. J., III; Lectka, T. “Column Asymmetric Catalysis for beta-Lactam Synthesis” Org. Lett. 2000, 2(25), 3963-3965 PDF
• Cox, C.; Lectka, T. “Synthetic Catalysis of Amide Isomerization” Acc. Chem. Res. 2000, 33(12), 849-858 PDF
• Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J., III; Lectka, T. “Catalytic, Asymmetric Synthesis of beta-Lactams” J. Am. Chem. Soc. 2000, 122(32), 7831-7832 PDF
• Wack, H.; Drury, W. J., III; Taggi, A. E.; Ferraris, D.; Lectka, T. “Nucleophilic Metal Complexes as Acylation Catalysts: Solvent-Dependent 'Switch' Mechanisms Leading to the First Catalyzed Staudinger Reaction” Org. Lett. 1999, 1(12), 1985-1988 PDF
• Cox, C.; Wack, H.; Lectka, T. “Nucleophilic Catalysis of Amide Isomerization” J. Am. Chem. Soc. 1999, 121(34), 7963-7964 PDF
• Cox, C.; Lectka, T. “Intramolecular Acid-Catalyzed Amide Isomerization in Aqueous Solution” Org. Lett. 1999, 1(5), 749-752 PDF
• Ferraris, D.; Young, B.; Dudding, T.; Drury, W. J., III; Lectka, T. “Catalytic, Enantioselective Alkylations of N,O- and N, N-Acetals and Hemiacetals” Tetrahedron 1999, 55(29), 8869-8882 PDF
• Cox, C.; Wack, H.; Lectka, T. “Strong Hydrogen Bonding to the Amide Nitrogen Atom in an 'Amide Proton Sponge': Consequences for Structure and Reactivity” Angew. Chem. Int. Ed. Engl. 1999, 38(6), 798-800 PDF
• Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. “Catalytic, Enantioselective Alkylations of N,O-Acetals” J. Org. Chem. 1999, 64(7), 2168-2169 PDF
• Drury, W. J., III; Ferraris, D.; Cox, C.; Young, B.; Lectka, T. “A Novel Synthesis of alpha-Amino Acid Derivatives through Catalytic, Enantioselective Ene-Reactions of alpha-Imino Esters” J. Am. Chem. Soc. 1998, 120(42), 11006-11007 PDF
• Cox, C.; Lectka, T. “Intramolecular Catalysis of Amide Isomerization: Kinetic Consequences of the 5-NH- -N_a Hydrogen Bond in Prolyl Peptides” J. Am. Chem. Soc. 1998, 120(41), 10660-10668 PDF
• Ferraris, D.; Young, B.; Cox, C.; Drury, W. J., III; Dudding, T.; Lectka, T. “Diastereoselective and Enantioselective Alkylation of alpha-Imino Esters with Enol Silanes Catalyzed by (R)-Tol-BINAP-CuClO₄(MeCN)₂” J. Org. Chem. 1998, 63(18), 6090-6091 PDF
• Ferraris, D.; Drury, W. J., III; Cox, C.; Lectka, T. "'Orthogonal' Lewis Acids: Catalyzed Ring Opening and Rearrangement of Acylaziridines” J. Org. Chem. 1998, 63(14), 4568-4569 PDF
• Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. “Catalytic, Enantioselective Alkylation of alpha-Imino Esters Using Late Transition Metal Phosphine Complexes as Catalysts” J. Am. Chem. Soc. 1998, 120(18), 4548-4549 PDF
• Cox, C.; Lectka, T. “Solvent Effects on the Barrier to Rotation in Carbamates” J. Org. Chem. 1998, 63(8), 2426-2427 PDF
• Ferraris, D.; Cox, C.; Anand, R.; Lectka, T. “C-F Bond Activation by Aryl Carbocations: Conclusive Intramolecular Fluoride Shifts between Carbon Atoms in Solution and the First Examples of Intermolecular Fluoride Ion Abstractions” J. Am. Chem. Soc. 1997, 119(18), 4319-4320 PDF
• Cox, C.; Young, V. G. Jr.; Lectka, T. “Intramolecular Catalysis of Amide Isomerization” J. Am. Chem. Soc. 1997, 119(9), 2307-2308. PDF
• Cox, C.; Ferraris, D.; Murthy, N. N.; Lectka, T. “Copper(II)-Catalyzed Amide Isomerization: Evidence for N-Coordination” J. Am. Chem. Soc. 1996, 118(22), 5332-5333 PDF