Publications

Meloche, J. L.; Ashfeld, B. L. “Development of a RhII-Catalyzed Formal [4+1]-Cycloaddition Toward Spirooxindole Pyrrolone Construction Employing Vinyl Isocyanates as 1,4-Dipoles” Angew. Chem. Int. Ed. 2017, Early View, DOI: 10.1002/anie.201701147. PDF

Thumbnail image of graphical abstract


Rodriguez, K. X.; Kaltwasser, N.; Toni, T. A.; Ashfeld, B. L. “Rearrangement of an Intermediate Cyclopropyl Ketene in a RhII-Catalyzed Formal [4+1]-Cycloaddition Employing Vinyl Ketenes as 1,4-Dipoles and Donor–Acceptor Metallocarbenes.” Org. Lett. 2017, ASAP, DOI: 10.1021/acs.orglett.7b00618. PDF


Rodriguez, K. X.; Vail, J. D.; Ashfeld, B. L. “Phosphine-Mediated Stereoconvergent [4+1] Cycloannulation of 1,2-Dicarbonyls and ortho-Quinone Methides: A Multicomponent Assembly of 2,3-Dihydrobenzofurans.” Org. Lett., 2016, 18 (18), 4514-4517. PDF


Higashi, D. L.; Biais, N.; Donahue, D. L.; Mayfield, J. A.; Tessier, C. R.; Rodriguez, K. X.; Ashfeld, B. L.; Luchetti, J.; Ploplis, V. A.; Castellino, F. J.; Lee, S. W. “Activation of Band 3 Mediates Group A Streptococcus Streptolysin S-Based β-Haemolysis.” Nat. Microbiol., 2016, 1 (2), 1-6. DOI:10.1038/nmicrobiol.2015.4. PDF


White, E. E.; Rodriguez, K. X.; Ashfeld, B. L. “Stereochemical Implications in the Synthesis of 3,3´-Spirocyclopropyl Oxindoles from β-Aryl/Alkyl-Substituted Alkylidene Oxindoles.” Tetrahedron, 2015, 71 (35), 5765-5775. PDF
*Invited article for the Symposium-in-Print in honor of Professor Barry M. Trost for receipt of the Tetrahedron Award for Creativity in Organic Synthesis.


Haugen, K. C.; Rodriguez, K. X.; Chavannavar, A. P.; Oliver, A. P.; Ashfeld, B. L. “Phosphine-Mediated Addition of 1,2-Dicarbonyls to Diazenes: An Umpolung Approach toward N-Acyl Hydrazone Synthesis.” Tetrahedron Lett. 2015, 56 (23), 3527-3530PDF
*Invited article for the Symposium-in-Print in honor of Professor Harry Wasserman.


Gianino, J. B.;
Campos, C. A.; Lepore, A. J.; Pinkerton, D. M.; Ashfeld, B. L. “Redox and Lewis Acid Relay Catalysis: A Titanocene/Zinc Catalytic Platform in the Development of Multicomponent Coupling Reactions.” J. Org. Chem. 2014, 79 (24), 12083-12095. PDF
*Invited manuscript for the special issue titled Mechanisms in Metal-Based Organic Chemistry.


Chavannavar, A. P.; Oliver, A. G.; Ashfeld, B. L. “An Umpolung Approach Toward N-Aryl Nitrone Construction: Phosphine-Mediated Addition of 1,2-Dicarbonyls to Nitroso Electrophiles.” Chem. Commun. 2014, 50 (74), 10853-10856PDF

Graphical abstract: An umpolung approach toward N-aryl nitrone construction: a phosphine-mediated addition of 1,2-dicarbonyls to nitroso electrophiles


Meloche, J. L.; Vednor, P. T.; Gianino, J. B.; Oliver, A. G.; Ashfeld, B. L. “Titanocene-Catalyzed Metallation of Propargylic Acetates in Homopropargylic Alcohol Synthesis.” Tetrahedron Lett., 2014, 55 (36), 5025-5028. PDF


Campos, C. A.; Gianino, J. B.; Bailey, B. J.; Baluyut, M. E.; Wiek, C.; Hanenberg, H.; Shannon, H.; Pollok, K. E.; Ashfeld, B. L. “Design, Synthesis, and Evaluation of Curcumin-Derived Arylheptanoids for Glioblastoma and Neuroblastoma Cytotoxicity.” Bioorg. Med. Chem. Lett. 2013, 23 (24), 6874-6878. PDF


Vogt, M.; Wu, C.; Oliver, A. G.; Schneider, W. F.; Ashfeld, B. L. “Site Specific Carboxylation of Abnormal Anionic NHeterocyclic Dicarbenes with CO2.” Chem. Commun. 2013, 49 (98), 11527-11529PDF

Graphical abstract: Site specific carboxylation of abnormal anionic N-heterocyclic dicarbenes with CO2


Lee, D.; Zhang, C.; Wei, C.; Ashfeld, B. L.; Gao, H. “Developing Hierarchically Porous Polypyrrole Materials for Fast and Efficient CO2 Capture.” J. Mater. Chem. A. 2013, 1 (47), 14862-14867. PDF

Graphical abstract: Hierarchically porous materials via assembly of nitrogen-rich polymer nanoparticles for efficient and selective CO2 capture


Fleury, L. M.; Wilson, E. E.; Vogt, M.; Fan, T. J.; Oliver, A. G.; Ashfeld, B. L. “An Amine-Free Approach Toward NToluenesulfonyl Amidine Construction: A Phosphite-Mediated Beckmann-Like Ligation of Oximes and Azides.” Angew. Chem. Int. Ed. 2013, 52 (44), 11589-11593. PDF

original image


Vogt, M.; Bennett, J. E.; Huang, Y.; Wu, C.; Brennecke, J. F.; Schneider, W. F.; Ashfeld, B. L. “Solid State Covalent Capture of CO2 Using N-Heterocyclic Carbenes.” Chem. Eur. J. 2013, 19 (34), 11134-11138. PDF
*Highlighted as a Frontispiece article in Chem. Eur. J. 2013, 19 (34), 11104-11114.
*Featured in Chemistry Views: Jones, K. “Capture of Carbon Dioxide with N-Heterocyclic Carbenes” October 3, 2013. Link


Lepore, A. J.; Pinkerton, D. M.; Ashfeld, B. L. “Relay Redox and Lewis Acid Catalysis in the Titanocene-Catalyzed Multicomponent Assembly of 1,5-Enynes.” Adv. Synth. Catal. 2013, 355, 1500-1504. PDF


Campos, C. A.; Gianino, J. B.; Ashfeld, B. L. “Bifunctional Titanocene Catalysis in Multicomponent Couplings: A Convergent Assembly of β-Alkynyl Ketones.” Org. Lett. 2013, 15 (11), 2656-2659. PDF
*Featured in the 2013 edition of Synfacts: Knochel, P.; Samann, C. “Synthesis of β-Alkynyl Ketones via TiCatalyzed Three-Component Coupling” Synfacts, 2013, 9 (9), 0993.


Meyer, C. J.; Vogt, M.; Catalino, J.; Ashfeld, B. L., “Synthesis of N-Heterocyclic Anionic Ionic Liquids from Functionalized Phosphonium Halides.” Synlett. 2013, 24, 1428-1432. PDF


Fleury, L. M.; Kosal, A. D.; Masters, J. T.; Ashfeld, B. L., “Cooperative Phosphine and Titanocene Catalysis: Accelerated C–X Activation for Efficient Generation of Reactive Organometallics.” J. Org. Chem. 2013, 78 (2), 253-269. PDF


Kosal, A. D.; Ashfeld, B. L. “N-(Benzyloxycarbonyloxy)-5-norbene-2,3-dicarboximide” Encyclopedia of Reagents for Organic Synthesis. 2013, DOI: 10.1002/047084289X.rn01521. Link


Kosal, A. D.; Ashfeld, B. L. “N-(tert-Butyloxycarbonyloxy)-5-norbene-2,3-dicarboximide” Encyclopedia of Reagents for Organic Synthesis. 2013, DOI: 10.1002/047084289X.rn01520. Link


Gianino, J. B.; Ashfeld, B. L., “Titanocene-Catalyzed Multicomponent Coupling Approach To Diarylethynyl Methanes.” J. Am. Chem. Soc. 2012, 134 (44), 18217–18220. PDF
*Featured as a “Synfact of the Month” in the 2013 edition of Synfacts: Knochel, P.; Samann, C. “Synthesis of Diarylethynyl Methanes via a Multicomponent Coupling” Synfacts, 2013, 9 (2), 0195.


Kosal, A. D.; Wilson, E. E.; Ashfeld, B. L., “Phosphine-Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides.” Angew. Chem. Int. Ed. 2012, 51 (48), 12036-12040. PDF

*Featured as a SynStory in the April 2013 issue of SynForm: Kosal, A. D.; Wilson, E. E.; Ashfeld, B. L., “Phosphine-Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides.” Zanda, M. Ed., SYNFORM, 2013/04, A44-A46, DOI: 10.1055/s-0032-1318334.
*Featured in Organic Highlights on the Organic Chemistry Portal: Lambert, T. H. “Functional Group Interconversion” May 13, 2013. Link

original image


Kosal, A. D.; Wilson, E. E.; Ashfeld, B. L., “Direct Acyl Substitution of Carboxylic Acids: A Chemoselective O-to-N Acyl Migration in the Traceless Staudinger Ligation.” Chem. Eur. J. 2012, 18 (45), 14444-14453. PDF

*Featured in Chemistry Views: Jones, K. “A Humdinger of a Staudinger” November 2012Link
 

Fleury, L. M.; Gianino, J. B.; Ashfeld, B. L., “Positional Chemoselectivity in the Zn(II)-Mediated Removal of Phenol Protecting Groups.” Tetrahedron Lett. 2012, 53, 5376-5379. PDF


Campos, C. A.; Ashfeld, B. L. “Dichlorobis(cyclopentadienyl) titanium – isobutylmagnesium halide.” 2012, Encyclopedia of Reagents for Organic Synthesis [Online], John Wiley & Sons Ltd., DOI: 10.1002/047084289X.rn01432. Link
 

Campos, C. A.; Gianino, J. B.; Pinkerton, D. M.; Ashfeld, B. L., “Aryl Aldehydes as Traceless Dielectrophiles in Bifunctional Titanocene-Catalyzed Propargylic C–X Activations.” Org. Lett. 2011, 13, 5680-5683. PDF
*Featured in the 2012 edition of Synfacts: Knochel, P.; Barl, N. M. “Aldehydes in Bifunctional TitanoceneCatalyzed Propargylic C-X Activations” Synfacts, 2012, 8 (1), 0082.


Wilson, E. E.; Oliver, A. G.; Hughes, R. P.; Ashfeld, B. L., “Synthesis of Phosphine-Ligated Zinc Acetylide Dimers: Enhanced Reactivity in Carbonyl Additions.” Organometallics. 2011, 30, 5214-5221. PDF


Fleury, L. M.; Ashfeld, B. L. “Generation of Allyl Grignard Reagents via Titanocene-Catalyzed Activation of Allyl Halides.” Tetrahedron Lett. 2010, 51, 2427-2430. PDF
*Featured in Organic Highlights on the Organic Chemistry Portal: Taber, D. F. “New Methods for C-C Bond Construction” February 21, 2010. Link


Kosal, A. D.; Ashfeld, B. L. “Titanocene-Catalyzed Conjugate Reduction of α,β-Unsaturated Carbonyl Derivatives.” Org. Lett. 2010, 12, 44-47. PDF
*Featured in the 2010 edition of Synfacts: Knochel, P.; Gavryushin, A. “Titanocene-Catalyzed 1,4-Reduction of α,β-Unsaturated Carbonyl Compounds” Synfacts, 2010, 2010 (3), 0344.


Fleury, L. M.; Ashfeld, B. L. “Organozinc Generation via the Titanium-Catalyzed Activation of Alkyl Halides.” Org. Lett. 2009, 11, 5670-5673. PDF

WORK CONDUCTED PREVIOUS TO B. L. ASHFELD’S APPOINTMENT AS ASSISTANT PROFESSOR OF CHEMISTRY AT THE UNIVERSITY OF NOTRE DAME

Trost, B. M.; Ashfeld, B. L. “Coupling of Alkenes and Alkynes: Synthesis of the C1-C11 and C18-C28 Fragments of Miyakolide.” Org. Lett. 2008, 10, 1893-1896. PDF


Ashfeld, B. L.; Miller, K. A.; Smith, A. J.; Tran, K; Martin S. F. “Features and Applications of [Rh(CO)2Cl]2-Catalyzed Alkylations of Unsymmetrical Allylic Substrates.” J. Org. Chem. 2007, 72, 9018-9031. PDF


Ashfeld, B. L.; Martin S. F. “Enantioselective Total Syntheses of Tremulenediol A and Tremulenolide A.” Tetrahedron. 2006, 62, 10497-10506. PDF


Ashfeld, B. L.; Judd, A. S. “Chloro(1,5-cyclooctadiene)rhodium(I) Dimer.” 2006, Encyclopedia of Reagents for Organic Synthesis [Online], John Wiley & Sons Ltd., DOI: 10.1002/047084289X.rn00699. Link


Ashfeld, B. L.; Martin S. F. “Enantioselective Syntheses of Tremulenediol A and Tremulenolide A.” Org. Lett. 2005, 7, 4535-4537. PDF


Ashfeld, B. L.; Miller, K. A.; Smith, A. J.; Tran, K; Martin S. F. “[Rh(CO)2Cl]2-Domino Reactions Involving Allylic Substitution and Subsequent Carbocyclization Reactions.” Org. Lett. 2005, 7, 1661-1663. PDF


Ashfeld, B. L.; Miller, K. A.; Martin S. F. “Direct Stereoselective Substitution in [Rh(CO)2Cl]2-Catalyzed Allylic Alkylations of Unsymmetrical Substrates.” Org. Lett. 2004, 6, 1321-1324. PDF