- Associate Professor
1567 Irving Hill Rd
Lawrence, KS 66045
- Synthetic Methodology
- Transition Metal Catalysis
- Physical Organic Chemistry
One of the directions of our research concerns the development of a novel family of chiral ligands employing a rigid cyclopropyl backbone for asymmetric transition metal catalysis. Significant conformational constrains and a well defined geometry make a three-membered carbocycle a unique, light weight, and rigid ligand platform capable of efficient stereo- and regiocontrol. This project integrates synthetic and theoretical approaches and invovles the elaboration of new methodologies towards phosphorous-containing cyclopropanes, synthesis of organometallic complexes, and development of new catalytic processes utilizing novel catalysts.
Another aspect of this project stems from the fact that some nucleotide mimics possessing a cyclopropyl phosphorous fragment exhibit potent antiviral and antimalarial activities. Accordingly, development of synthetic methodologies towards phosphorous-containing cyclopropanes is also aimed at expanding the pool of versatile cyclopropylphosphonate derivatives available for biological screening and providing additional tools for structure optimization en route to more selective drug candidates.
In the frame of a multidisciplinary project initiated by the Center of Environmentally Beneficial Catalysis, our group is involved in the design and development of new, environmentally benign transition metal-catalyzed processes for manufacturing of commodity and specialty chemicals. This includes synthesis and testing of new catalyst systems, optimization of reaction conditions, and adaptation of existing transition metal-catalyzed methodologies to CO2-expanded organic and ionic liquid media. One of the examples of such processes, currently being developed in our laboratories, is the synthesis of non-steroidal anti-inflammatory drugs via the Rh-catalyzed asymmetric hydroformylation and Mn-catalyzed oxidation in aqueous media.
Selected Publications —
Prosser, Anthony R.; Banning, Joseph E.; Rubina, Marina; Rubin, Michael Formal Nucleophilic Substitution of Bromocyclopropanes with Amides en route to Conformationally Constrained β-Amino Acid Derivatives. Organic Letters (2010), 12(18), 3968-3971.
Kim, Ryan.; Sherrill, W. M.; Rubin, M. Ring-Retentive Deprotonation of Cyclopropene-3-Carboxamides. Tetrahedron (2010), 66(27-28), 4947-4953.
Banning, Joseph E.; Prosser, Anthony R.; Rubin, M. Thermodynamic Control of Diastereoselectivity in the Formal Nucleophilic Substitution of Bromocyclopropanes. Organic Letters (2010), 12(7), 1488-1491.
Alnasleh, Bassam K.; Sherrill, William M.; Rubina, Marina; Banning, Joseph; Rubin, Michael. Highly Diastereoselective Formal Nucleophilic Substitution of Bromocyclopropanes. Journal of the American Chemical Society (2009), 131(20), 6906-6907.
Sherrill, William M.; Kim, Ryan; Rubin, Michael. Synthesis of Cyclopropenes via 1,2-Elimination of Bromocyclopropanes Catalyzed by Crown Ether. Synthesis (2009), (9), 1477-1484.
Rubina, Marina; Sherrill, William M.; Rubin, Michael. Dramatic Stereo- and Enantiodivergency in the Intermolecular Asymmetric Heck Reaction Catalyzed by Palladium Complexes with Cyclopropane-Based PHOX Ligands. Organometallics (2008) 27(24), 6393-6395.
Sherrill, William M.; Rubin, Michael. Rhodium-Catalyzed Hydroformylation of Cyclopropenes. Journal of the American Chemical Society (2008), 130(41), 13804-13809.