Biography:

1993-1997   B.Sc., Dublin City University.
1997-2000   Ph.D., (with Prof. A. F. Hegarty), University College Dublin.
2001-2003   Alexander von Humboldt Fellow (with Prof. Dr. S. Blechert), Technische Universität Berlin.
2003           Appointed to the staff at Trinity College Dublin.

Research Projects:

Our group’s research interests are concentrated on the discovery of new synthetic methodologies with a focus on new catalyst design and synthesis.

Organocatalysts- small enzyme mimics

The development of small metal-free molecules capable of catalysing chemical reactions is (in our opinion) one of the most challenging and rewarding fields in contemporary organic chemistry. We are interested in the development of chiral nucleophilic organocatalysts capable of promoting simple transformations of racemic substrates with high levels of asymmetric induction. Examples include -

1. Nucleophilic catalysis

We are interested in the development of chiral nucleophilic organocatalysts capable of promoting simple transformations of racemic (or achiral) substrates with high levels of asymmetric induction. In particular we are engaged in the development of chiral 4-dimethylaminopyridine analogues for use in a wide range of processes, including the kinetic resolution of racemates, the efficient asymmetric synthesis of molecules of biological and pharmaceutical interest and polymer synthesis. Early studies have led to the design of a chiral nucleophilic catalyst which can mimic enzymatic action by changing conformation on binding to its substrate (induced-fit model), which allows remote chiral information to influence the stereochemical course of the catalytic process. This design strategy allows chiral information to be transferred from catalyst to substrate in a controlled fashion that does not (as has often traditionally been the case) slow the reaction rate considerably.

2. Bifunctional catalysts - simultaneous activation of electrophilic and nucleophilic reaction components

The group is also pursuing the synthesis and evaluation of novel bifunctional catalysts that mimic another facet of enzymatic action - the ability to act as both a Lewis-acid and a Lewis-base simultaneously. These catalysts are potentially very useful molecules of broad scope, with applications in cycloaddition processes and nucleophilic addition chemistry.






New synthetic methodology

We are interested in the development of new organocatalytic reactions and have recently discovered a novel tertiary-amine-catalysed hydroalkoxylation reaction of activated alkenes and alkynes that is operationally simple which requires minimal product purification. Thusfar we have demonstrated its application in a one-pot synthesis of a natural product (a Monarch butterfly pheromone) and in the facile preparation of monoprotected 1,3-dicarbonyl materials (see below). These reactions provide useful alternative routes to synthetically important -oxygenated carbonyl compounds more usually prepared via aldol chemistry.






Anti-cancer drug design

Paullones are tetracyclic indole-based compounds that have been demonstrated to act as powerful cyclin-dependent kinase (CDK) inhibitors with potential anti-tumour properties. These relatively new drug-candidates have yet to be fully developed as targets for anti-cancer drug-design. We (in collaboration with Dr. D. H. Grayson) are engaged in the design of a range of paullone derivatives, with the dual-aim of both maximising CDK1 binding selectivity and in vivo activity.

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Current Group Members:

Ph.D. Students: -

Seamus McCooey,		B. A. (Mod.) TCD 2003,		email: mccooeys@tcd.ie		extn. 1601
Ciaran Ó Dálaigh,		B. A. (Mod.) TCD 2003,		email: odalaigc@tcd.ie		extn. 1601
Eimear Fleming,		B. A. (Mod.) TCD 2004,		email: fleminge@tcd.ie		extn. 1601
David Power,		B. A. (Mod.) TCD 2004,		email: powerdp@tcd.ie		extn. 1601
Barbara Procuranti,		Laurea. University of Pisa 2004		email: procurab@tcd.ie		extn. 1601
Sarah O'Toole,		B.Sc. DCU 2003		email: otooles2@tcd.ie		extn. 1601
Conor Noonan,		B. A. (Mod.) TCD 2005		email: noonanc@tcd.ie		extn. 1601

Former Group Members:

Dr. Declan Maher		2003		(Postdoc) - Helsinn
Dr. Stephen Hynes		2004		(Postdoc)
Conny Faltin,		2004		(Diplomaarbeiter) - Ph.D. student, T.U. Berlin
Julie Murtagh		2004		(Summer Student) - Ph.D. Student, U.C.D.
Bernie Moore		2005		(Summer Student) - Postgraduate Student, T.C.D.
Patrick Nagle		2005		(Summer Student)
Louise Ray		2005		(Summer Student)

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Publications:

22.		'Chiral phosphoric acids: powerful organocatalysts for asymmetric addition reactions to imines', S. J. Connon, Angew. Chem. Int. Ed., 2006, 45, accepted (DOI: 10.1002/anie.200600529).
21.		Organocatalysis mediated by (thio)urea derivatives', S. J. Connon, Chem. Eur. J., 2006, 12, accepted (DOI: 10.1002/chem.200501076)
20.		'Catalytic asymmetric acyl-transfer mediated by chiral pyridine derivatives', S. J. Connon, Lett. Org. Chem., 2006, 3, accepted
19.		'Urea- and thiourea-substituted cinchona alkaloid derivatives as highly efficient bifunctional organocatalysts for the asymmetric addition of malonate to nitroalkenes: inversion of configuration at C9 dramatically improves catalyst performance.' S. H. McCooey and S. J. Connon, Angew. Chem. Int. Ed. 2005, 44, 6367.
18.		'Kinetic resolution of sec-alcohols using a new class of readily assembled (S)-proline-derived 4-(pyrrolidino)-pyridine analogues', C. Ó Dálaigh, S. J. Hynes, D. J. Maher and S. J. Connon, Org. Biomol. Chem., 2005, 3, 981.
17.		'Novel amine-catalysed hydroalkoxylation reactions of alkenes and alkynes', J. E. Murtagh, S. H. McCooey and S. J. Connon, Chem. Commun. 2005, 227.
16.		'Acrylamide in the Baylis-Hillman reaction: expanded reaction scope and the unexpected superiority of DABCO over more basic tertiary amine catalysts', C. Faltin, E. M. Fleming and S. J. Connon, J. Org. Chem., 2004, 69, 6496
15.		'Acceleration of the DABCO-promoted Baylis-Hillman reaction using a recoverable H-bonding organocatalyst', D. J. Maher and S. J. Connon, Tetrahedron Lett., 2004, 45, 1301.
14.		'Stabilised 2,3-pyridyne reactive intermediates of exceptional dienophilicity' , S. J. Connon and A. F. Hegarty, Eur. J. Org. Chem., 2004, 3477.
13.		'A highly active and readily recyclable olefin metathesis catalyst', S. J. Connon, A.M. Dunne and S. Blechert, Catalysts for Fine Chemical Synthesis (Wiley Interscience - Ed. - S. Roberts), 2004, Vol. 3, 174.
12.		'Recent advances in alkene metathesis', S. J. Connon and S. Blechert, Topics In Organometallic Chemistry (Springer Verlag - Ed. P. Dixneuf) 2004, 11, 93.
11.		'Ruthenium olefin metathesis catalysts with modified styrene ethers: influence of steric and electronic effects' M. Zaja, S. J. Connon, A. M. Dunne, M. Rivard, N. Buschmann, J. Jiricek and S. Blechert, Tetrahedron, 2003, 59, 6545.
10.		'Practical olefin metathesis in protic media under an air atmosphere', S. J. Connon, M. Rivard, M. Zaja and S. Blechert', Adv. Syn. Catal., 2003, 345, 572.
9.		'Recent developments in olefin cross metathesis', S. J. Connon and S. Blechert, Angew. Chem. Int. Ed. Engl., 2003, 42, 1900.
8.		'Novel metathesis catalysts', S. J. Connon, S. Blechert, and BASF AG, German patent. DE 10234810.3., 2002,EU patent 03016465.1, 2003.
7.		'A self-generating and recyclable polymer-bound olefin metathesis catalyst', S. J. Connon, A. M. Dunne and S. Blechert, Angew. Chem. Int. Ed. Engl., 2002, 114, 3835.
6.		'A mechanism switch in enyne metathesis reactions involving rearrangement: Influence of heteroatoms in the propargylic position', N. Lucas, S. Randl, S. J. Connon and S. Blechert, Adv. Syn. Catal., 2002, 344, 631.
5.		'A polymer-supported phosphine-free ruthenium alkylidene for olefin metathesis in methanol and water", S. J. Connon and S. Blechert, Bioorg. Med. Chem. Lett., 2002, 12, 1873.
4.		'Ring-opening cross metathesis of unstrained cycloalkenes', S. Randl, S. J. Connon and S. Blechert, Chem. Commun., 2001, 1796.
3.		'Highly efficient and recyclable polymer-bound catalyst for olefin metathesis reactions', S. Randl, N. Buschmann, S. J. Connon and S. Blechert, Synlett, 2001, 1547.
2.		'Diels-Alder cycloadditions of stabilised 2,3-pyridynes', A. F. Hegarty and S. J. Connon, Tetrahedron Lett., 2001, 42, 735.
1.		'Substituted 3,4-pyridynes: clean cycloadditions', A. F. Hegarty and S. J. Connon, J. Chem. Soc. Perkin Trans. 1, 2000, 1245.

Any queries about this page should go to Dr. Stephen Connon.
Last updated 28th February, 2006 by Teresa Lalor.