Fillion Synthetic Organic/Organometallic Research Group


University of Waterloo, Waterloo, Ontario, Canada







Carbon-Based Leaving Group in Substitution Reactions: Functionalization of sp3-Hybridized Quaternary and Tertiary Benzylic Carbon Centers

Stuart Mahoney, Tiantong Lou, Ganna Bondarenko and Eric Fillion

                Org. Lett. ASAP





N-Fused Indolines through Non-Carbonyl Stabilized Rhodium Carbenoid C-H Insertion of N-Aziridinyl Imines

Stuart Mahoney and Eric Fillion

                Chem. Eur. J. 2012, 18, 68-71






Catalytic Intramolecular Friedel-Crafts Reaction of Benzyl Meldrum’s Acid Derivatives: Preparation of 5,6-Dimethoxy-2-Methyl-1-Indanone

Tiantong Lou, E-Ting Liao, Ashraf Wilsily and Eric Fillion

                Org. Synth. 2012, 89, 115-125







Meldrum’s Acids and 5-Alkylidene Meldrum’s Acids in Catalytic Carbon-Carbon Bond-Forming Processes

Aaron M. Dumas and Eric Fillion

                Acc. Chem. Res. 2010, 43, 440-454







Asymmetric Addition of Alkenylstannanes to Alkylidene Meldrum’s Acids

Stuart J. Mahoney, Aaron M. Dumas and Eric Fillion

                Org. Lett. 2009, 11, 5346-5349





Asymmetric Synthesis of All-Carbon Benzylic Quaternary Stereocenters via Conjugate Addition to Alkylidene and Indenylidene Meldrum’s Acids

Ashraf Wilsily and Eric Fillion

                                                                J. Org. Chem. 2009, 74, 8583-8594





Hydrogenolysis of Unstrained Carbon-Carbon sigma-Bonds-Stereoselective Entry Into Benzylic Tertiary Centers

Ashraf Wilsily, Yen Nguyen, and Eric Fillion

                J. Am. Chem. Soc. 2009, 131, 15606-15607





Enantioselective Rhodium-Catalyzed Conjugate Alkynylation of 5-Benzylidene Meldrum’s Acids with TMS-acetylene

Eric Fillion and Alexander K. Zorzitto

                J. Am. Chem. Soc. 2009, 131, 14608-14609  



Functionalization of Csp3-H Bond- Sc(OTf)3-Catalyzed Domino 1,5-Hydride Shift/Cyclization/Friedel-Crafts Acylation Reaction of Benzylidene Meldrum’s Acids

Stuart J. Mahoney, David T. Moon, Jon Hollinger, and Eric Fillion

                Tetrahedron Letters 2009, 50, 4706-4709


Description: Description: Description: stuabs


Scandium Triflate-Catalyzed Intramolecular Friedel-Crafts Acylation with Meldrum’s Acids: Insight into the Mechanism

Eric Fillion and Dan Fishlock

                Tetrahedron 2009, 65, 6682-6695 (invited contribution to special issue in honour of Prof. Larry Overman)




Enantioselective Copper-Catalyzed Conjugate Addition of Dimethylzinc to 5-(1-Arylalkylidene) Meldrum’s Acids

Ashraf Wilsily, Tiantong Lou and Eric Fillion

                Synthesis 2009, 2066-2072 (invited contribution to special issue on phosphoramidite ligands)



Palladium-Catalyzed Intramolecular Reactions of (E)-2,2-Disubstituted 1-Alkenyldimethylalanes with Aryl Triflates

Eric Fillion, Vincent É. Trépanier, Jarkko J. Heikkinen, Anna A. Remorova, Rebeka J. Carson, Julie M. Goll and Adam Seed

                Organometallics 2009, 28, 3518-3531



Sc(OTf)3-Catalyzed Conjugate Allylation of Alkylidene Meldrum’s Acids

Aaron M. Dumas and Eric Fillion

                Org. Lett. 2009, 11, 1919-1922





Probing Persistent Intramolecular C-H···X (X = O, S, Br, Cl, and F) Bonding in Solution Using Benzyl Meldrum’s Acid Derivatives

Eric Fillion, Ashraf Wilsily and Dan Fishlock

                J. Org. Chem. 2009, 74, 1259-1267





Tuning the Reactivity of Palladium Carbenes Derived from Diphenylketene

Julie M. Goll and Eric Fillion

                Organometallics, 2008, 27, 3622-3625



Asymmetric Synthesis of Carboxylic Acid Derivatives Having an All-Carbon α-Quaternary Center through Cu-Catalyzed 1,4-Addition of Dialkylzinc Reagents to 2-Aryl Acetate Derivatives

Ashraf Wilsily and Eric Fillion

                Org. Lett. 2008, 10, 2801-2804



Synthesis of Fused 4,5-Disubstituted Indole Ring Systems by Intramolecular Friedel-Crafts Acylation of 4-Substituted Indoles

Eric Fillion and Aaron M. Dumas

                J. Org. Chem. 2008, 73, 2920-2923



Sequential Rh(I)/Pd-Catalyzed 1,4-Addition/Intramolecular Allylation: Stereocontrolled Construction of gamma-Butyrolactones and Cyclopropanes

Eric Fillion, Sébastien Carret, Lauren G. Mercier, and Vincent É. Trepanier

                Org. Lett. 2008, 10, 437-440




Ambiphilic Vinylcarbenoid Reactivity of (α-(Tributylstannyl)-π-allyl)palladium(II) Species

Vincent É. Trepanier and Eric Fillion

                Organometallics 2007, 26, 30-32



A General and Practical Preparation of Alkylidene Meldrum’s Acids

Aaron M. Dumas, Adam Seed, Alexander K. Zorzitto, and Eric Fillion

                Tetrahedron Lett. 2007, 48, 7072-7074




Asymmetric Cu-Catalyzed 1,6-Conjugate Addition of Dialkylzinc Reagents to 5-(3-Aryl-2-propenylidene) Meldrum’s Acids

Eric Fillion, Ashraf Wilsily, and E-Ting Liao

                Tetrahedron: Asymmetry 2006, 17, 2957-2959



Modular Synthesis of Tetrahydrofluorenones from 5-Alkylidene Meldrum’s Acids

Eric Fillion, Aaron M. Dumas, and Sylvia A. Hogg

                J. Org. Chem. 2006, 71, 9899-9902



Asymmetric Synthesis of All-Carbon Benzylic Quaternary Stereocenters via Cu-Catalyzed Conjugate Addition of Dialkylzinc Reagents to 5-(1-Arylalkylidene) Meldrum's Acids

Eric Fillion and Ashraf Wilsily

                J. Am. Chem. Soc. 2006, 128, 2774-2775



Yb(OTf)3-Catalyzed Reactions of 5-Alkylidene Meldrum's Acids with Phenols - One-Pot Assembly of 3,4-Dihydrocoumarins, 4-Chromanones, Coumarins, and Chromones

Eric Fillion, Aaron M. Dumas, Bryan A. Kuropatwa, Neil R. Malhotra, and Tamsyn C. Sitler.

J. Org. Chem. 2006, 71, 409-412




Total Synthesis of (±)-Taiwaniaquinol B via a Domino Intramolecular Friedel-Crafts Acylation/Carbonyl a-tert-Alkylation Reaction

Eric Fillion  and Dan Fishlock

J. Am. Chem Soc. 2005, 127, 13144-13145



Meldrum's Acids as Acylating Agents in the Catalytic Intramolecular Friedel-Crafts Reaction
Eric Fillion, Dan Fishlock, Ashraf Wilsily, and Julie M. Goll

            J. Org. Chem. 2005,70, 1316



Oxidative coupling of 2-substituted 1,2-dihydro-1-naphthols using Jones reagent: a simple entry into 3,3′-disubstituted 1,1′-binaphthyl-4,4′-diols

Eric Fillion, Vincent E. Trépanier, Lauren G. Mercier, Anna A. Remorova and Rebekah J. Carson

            Tetrahedron Lett. 2005, 46, 1091-1094





Palladium-Catalyzed Carbon-Carbon Bond Forming 1,2-Ligand Migration of Organoalanes

Eric Fillion, Rebekah J. Carson, Vincent E. Trépanier, and Julie M. Goll

J. Am. Chem. Soc. 2004, 126, 15354-15355





Cine Substitution in the Stille Coupling: Evidence for the Carbenoid Reactivity of sp3-gem-Organodimetallic Iodopalladio-trialkylstannylalkane Intermediates

Eric Fillion and Nicholas J. Taylor

J. Am. Chem. Soc. 2003, 125, 12700-12701



Efficient and Expedient Two-Step Pyranose-Retaining Fluorescein-Conjugation of Complex Reducing Oligosaccharides: Galectin Oligosaccharide Specificity Studies in a Fluorescence Polarization Assay

Christopher T. Öberg, Susanne Carlsson, Eric Fillion, Hakon Leffler, and Ulf J. Nilsson

Bioconjugate Chem. 2003, 14, 1289-1297



Convenient Access to Polysubstituted 1-Indanones by Sc(OTf)3-Catalyzed Intramolecular Friedel-Crafts Acylation of Benzyl Medrum's Acid Derivatives

Eric Fillion and Dan Fishlock

Org. Lett. 2003, 5, 4653-4656



Enantioselective Synthesis of Bicyclo[6.1.0]nonane-9-Carboxylic Acids via Me2AlOTf-Promoted Intramolecular Friedel-Crafts Alkylation of Arenes with the g-Lactone Moiety of 3-Oxa-Bicyclo[3.1.0]hexan-2-Ones

Eric Fillion and Rachel L. Beingessner

J. Org. Chem. 2003, 68, 9485-9488