Navigation

Researchers at UCD

researcher

Michael Casey

Senior Lecturer

School Of Chemistry & Chemical Biology
Science Centre - South
Belfield
Dublin 4

Tel: +353 1 7162420
Email: mike.casey@ucd.ie

Biography

1975 - 1979 B.Sc., UCC, First Class Honours in Chemistry.
1979 - 1982 PhD, Imperial College, London, with C.W. Rees and C. J. Moody.
1982-1984 Postdoctoral associate, Columbia University, New York, with G. Stork
1984-1992 Lecturer, University of Salford
1992-2004 Lecturer in Organic Chemistry, UCD
2005-present Senior lecturer in Organic Chemistry, UCD

Professional

         

Conference Contributions

Casey M.; (2003) Rivals for Oxazolines: Preparation and Applications of Imidazoline Ligands. [Oral Presentation], 19th International Congress in Heterocyclic Chemistry, Fort Collins, Colorado , 14-AUG-03.
Casey M.; (2001) Imidazolines: versatile new ligands for asymmetric catalysis. [Invited Lecture], COST D24 Workshop, University of Lille , 16-NOV-01.
Casey, M.; (2001) Imidazolines: versatile new ligands for asymmetric catalysis. [N/A], Young Synthetic Chemists Meeting, Univ. Wales , 30-SEP-01 - 30-SEP-01.
*; (2001) Imidazolines: versatile new ligands for asymmetric catalysis. [N/A], ESOC12, Groningen , 01-JUL-01 - 01-JUL-01.
Casey, M.; (1999) 'The Heck Reaction: Mechanistic Insights and Novel Ligands'. [N/A], OMCOS 10, Versailles , 01-JUL-99 - 01-JUL-99.
 

Employment

Employer: Columbia University, New York
Position: Post Doctoral Research
Employer: University of Salford
Position: College Lecturer
Employer: University College Dublin
Position: College Lecturer

Education

Year 1979 Institution:
Qualification: BSc Subject:
Year 1982 Institution: University of London
Qualification: PhD Subject:
Year Institution:
Qualification: DIC Subject:
         

Publications

Books

Casey, M. et al.; (1990) Advanced Practical Organic Chemistry. Glasgow: Blackie. [Details]

Book Chapters

Casey M.; (2005) 'Iminoacyl functions linked to any heteroatom other than halogen, chalcogen, or nitrogen' In: Katritzky A. R., Taylor R. J. K (eds). Comprehensive Organic Functional Group transformations II. , pp.701-724 [Details]
 

Peer Reviewed Journals

Grealis, JP,Muller-Bunz, H,Ortin, Y,Casey, M,McGlinchey, MJ (2013) 'Synthesis of Isobavachalcone and Some Organometallic Derivatives'. European Journal of Organic Chemistry, :332-347. [DOI] [Details]
Banide, E. V., Grealis, J. P., Mueller-Bunz, H., Ortin, Y., Casey, M., Mendicute-Fierro, C., Lagunas, M. C., McGlinchey, M. J., ; (2008) 'Chromium, iron, ruthenium and gold complexes of 3,3-(biphenyl-2,2 '-diyl)-1-diphenylphosphino-1-phenylallene: A versatile ligand'. Journal of Organometallic Chemistry, 693 (10):1759-1770. [Details]
Grealis, J. P., Muller-Bunz, H., Ortin, Y., Condell, M., Casey, M., McGlinchey, M. J., ; (2008) 'Birch reduction of hexaphenyl- and pentaphenylbenzene and an X-ray crystallography and NMR spectroscopy study of cis- and epi-1,2,3,4,5,6-hexaphenylcyclohexane and of 2,3,5,6-tetraphenyl-1,1 '-bicyclohexylidene: Cannizzaro's conundrum revisited'. Chemistry-A European Journal, 14 (5):1552-1560. [Details]
Grealis, J. P., Muller-Bunz, H., Casey, M., McGlinchey, M. J., ; (2008) 'Cannizzaro's (C7H6)(n) conundrum resolved: [1.1.1]orthocyclophane was first made 150 years ago'. Tetrahedron Letters, 49 (9):1527-1530. [Details]
Stork, G. et al.; (2005) 'Regiospecific and stereoselective syntheses of (+/-)-reserpine and (-)-reserpine'. Journal of the American Chemical Society, 127 (46):16255-16262. Available Online [Details]
M. Casey, N. A. Boland, S. J. Hynes, J. W. Matthews, H. Müller-Bunz, P. Wilkes; (2004) 'Preparation of Enantiopure Biimidazoline Ligands and Their Use in Asymmetric Catalysis'. Organic and Biomolecular Chemistry, 2 :1995-2002. [Details]
M. Casey, C. M. Keaveney; (2004) 'A Concise Stereocontrolled Formal Total Synthesis of (±)-Podophyllotoxin Using Sulfoxide Chemistry'. Chemical Communications, :184-185. [Details]
R. Appelbe, M. Casey, A. Dunne, E. Pascarella; (2003) 'Stereoselective Synthesis of Tetralins Using Cationic Cyclisations'. Tetrahedron Letters, 44 :7641-7644. [Details]
M. Casey, J. A. Donnelly, J. C. Ryan S. Ushioda; (2003) 'Synthesis of Bicyclic Lactams Using Novel Schmidt Reactions'. Arkivoc, (vii):310-327. [Details]
M. Casey, M. P. Smyth; (2003) 'Ligand Electronic Effects in Enantioselective Diethylzinc Additions'. Synlett, :102-106. [Details]
M. Casey, C. M. Keaveney, A. J. Walker; (2002) 'MIRC Reactions Using Sulfoxides and Synthesis of Dictyopterene A'. Arkivoc, (v):91-103. [Details]
Boland, NA; Casey, M; Hynes, SJ; Matthews, JW; Smyth, MP; ; (2002) 'A novel general route for the preparation of enantiopure imidazolines'. Journal of Organic Chemistry, 67 (11):3919-3922. [Details]
Appelbe, Z., Casey, M., Keaveney, C. M., and Kelly, C. J.; (2002) 'A Novel Method for the Stereoselective Synthesis of Tetralins and Indanes'. Synlett, . [Details]
Casey, M., Lawless, J., and Shirran, C.; (2000) 'The Heck Reaction: Mechanistic Insights and Novel Ligands'. Polyhedron, 19 :517-520. [Details]
Casey, M., Gairns, R. S., Geraghty, G. G., Kelly, C. J., Murphy, P. J., and Walker, A. J.; (2000) 'Highly Stereoselective Conjugate Additions of Heteroaryl Alkyl Sulfoxides'. Synlett, 1721 . [Details]
Casey, M., Gairns, R. S., and Walker, A. J.; (2000) 'Synthetically Useful Desulfurisation Reactions of Heteroaryl Sulfoxide Conjugate Adducts'. Synlett, 1725 . [Details]
                                                                                             

Research

Research Interests

Asymmetric catalysis

We are working on a family of nitrogen-containing compounds, imidazolines, which are easily tunable strong donors and bases. They have great potential as catalysts and ligands in a wide variety of enantioselective reactions. We have prepared a range of enantiopure imidazolines and bisimidazolines using a novel synthetic method developed in our group. We are now exploring their use in asymmetric catalysis and have obtained excellent results in some synthetically useful reactions. Changing the electronic properties and the conformational preferences of the imidazolines, by changing the N1-substituent (easily done using our new synthetic method), caused pronounced changes in the enantioselectivity of some reactions. The potential for easy tuning in this way is an advantage of imidazolines compared to the closely related oxazolines. Many imidazolines have notable biological activity, so the biological evaluation of our new imidazolines will also be of interest.

Organosulfur chemistry
We have a long term interest in developing new synthetic methods using organosulfur compounds. We carried the first systematic studies of the addition of sulfoxide-stabilised anions to a,b-unsaturated carbonyl compounds and obtained excellent stereoselectivity. New reactions, such as the stereoselective conversion of conjugate adducts into lactones and carbocycles, have been developed. The present focus of the research is on applications to total synthesis, particularly of podophyllotoxin, which is a precursor for important anticancer drugs. A short formal total synthesis of (±)-podophyllotoxin has been achieved and work on an enantioselective version is in progress.

Synthesis of biologically active targets
We have developed a new stereoselective method for forming tetralins and related compounds using cationic cyclisations. This reaction is being applied to the development of efficient syntheses of analogues of naturally occurring anti-cancer compounds, and of the pseudopterosins, which are potent anti-inflammatory agents. Some of this work is being carried out in collaboration with fellow members of the Conway Institute, who will test the compounds for biological activity and study their molecular mechanisms of action. We are also working on a novel route to the potent anti-muscarinic compound himbacine.