Nessan Kerrigan

Dr

Contact Details


X127

T: Ext. 5308
E: Nessan.Kerrigan@dcu.ie
Assistant Professor


E: nessan.kerrigan@dcu.ie
W: https://kerriganchemistry.com/

Biography

Nessan Kerrigan obtained his B.Sc. in Chemistry from University College Dublin (1992-1996).  He then completed his Ph.D. in Chemistry at University College Dublin (1996-2000) under the direction of Professor Declan G. Gilheany.  He spent a year in industry working as a process development chemist for Merck before carrying out postdoctoral research at the University of Glasgow (2002-2004) with Professor David J. Procter.  He carried out further postdoctoral research at the University of Pittsburgh (2004-2006) with Prof. Scott G. Nelson.  Dr. Kerrigan began his independent research career at Oakland University in 2006.  The Kerrigan group carries out research in the area of synthetic organic chemistry.  Most of their work is of the basic/fundamental chemistry research kind and is focused on the development of new efficient methods for the construction of biologically interesting organic molecules.  In August 2017, Dr. Kerrigan returned to Ireland to take up a position as Lecturer in the School of Chemical Sciences at Dublin City University.

Peer Reviewed Journals

  Year Publication
2019 'Asymmetric Synthesis of Tetrahydrofurans through Palladium(0)-Catalyzed [3 + 2]-Cycloaddition of Vinylcyclopropanes with Ketenes'
Mondal M.;Panda M.;McKee V.;Kerrigan N. (2019) 'Asymmetric Synthesis of Tetrahydrofurans through Palladium(0)-Catalyzed [3 + 2]-Cycloaddition of Vinylcyclopropanes with Ketenes'. Journal of Organic Chemistry, 84 (18):11983-11991 [DOI] [Details]
2019 'Asymmetric synthesis of cyclopentanones through dual Lewis acid-catalysed [3+2]-cycloaddition of donor-Acceptor cyclopropanes with ketenes'
Mondal M.;Panda M.;Davis N.;McKee V.;Kerrigan N. (2019) 'Asymmetric synthesis of cyclopentanones through dual Lewis acid-catalysed [3+2]-cycloaddition of donor-Acceptor cyclopropanes with ketenes'. Chemical Communications, 55 (90):13558-13561 [DOI] [Details]
2018 'Recent Developments in Vinylsulfonium and Vinylsulfoxonium Salt Chemistry'
Mukulesh Mondal, Shi Chen and Nessan J. Kerrigan (2018) 'Recent Developments in Vinylsulfonium and Vinylsulfoxonium Salt Chemistry'. Molecules, 23 (4) [DOI] [Details]
2017 'Asymmetric Synthesis of gamma-Lactones through Koga Amine-Controlled Addition of Enediolates to a,beta-Unsaturated Sulfoxonium Salts'
Peraino, NJ;Kaster, SH;Wheeler, KA;Kerrigan, NJ (2017) 'Asymmetric Synthesis of gamma-Lactones through Koga Amine-Controlled Addition of Enediolates to a,beta-Unsaturated Sulfoxonium Salts'. Journal of Organic Chemistry, 82 :606-615 [DOI] [Details]
2015 'Phosphine-catalyzed synthesis of beta-lactones from ketenes and chiral beta-oxyaldehydes'
Chen, S;Mondal, M;Adams, MP;Wheeler, KA;Kerrigan, NJ (2015) 'Phosphine-catalyzed synthesis of beta-lactones from ketenes and chiral beta-oxyaldehydes'. Tetrahedron Letters, 56 :6421-6424 [DOI] [Details]
2014 'Phosphine-catalyzed asymmetric synthesis of β-lactones from disubstituted ketenes and aldehydes'
Chen S;Mondal M;Ibrahim AA;Wheeler KA;Kerrigan NJ; (2014) 'Phosphine-catalyzed asymmetric synthesis of β-lactones from disubstituted ketenes and aldehydes'. Journal of Organic Chemistry, 79 (11) [DOI] [Details]
2014 'Regioselective synthesis of highly substituted enol esters from ketoketene dimer beta-lactones'
Salo, EC;Dayak, KR;Huxford, J;Wei, PH;Peraino, NJ;Kerrigan, NJ (2014) 'Regioselective synthesis of highly substituted enol esters from ketoketene dimer beta-lactones'. Arkivoc, :285-295 [DOI] [Details]
2014 'Asymmetric synthesis of gamma-lactones through reaction of sulfoxonium ylides, aldehydes, and ketenes'
Peraino, NJ;Ho, HJ;Mondal, M;Kerrigan, NJ (2014) 'Asymmetric synthesis of gamma-lactones through reaction of sulfoxonium ylides, aldehydes, and ketenes'. Tetrahedron Letters, 55 :4260-4263 [DOI] [Details]
2013 'Diastereoselective formation of beta-hydroxyketones by the reduction of Ketene dimers'
Wei, PH;Gary, MA;Nalla, D;Harzmann, GD;Ibrahim, AA;Dayak, KR;Kerrigan, NJ (2013) 'Diastereoselective formation of beta-hydroxyketones by the reduction of Ketene dimers'. Tetrahedron Letters, 54 :932-935 [DOI] [Details]
2013 'Diastereoselective Reaction of Sulfoxonium Ylides, Aldehydes and Ketenes: An Approach to trans-gamma-Lactones'
Mondal, M;Ho, HJ;Peraino, NJ;Gary, MA;Wheeler, KA;Kerrigan, NJ (2013) 'Diastereoselective Reaction of Sulfoxonium Ylides, Aldehydes and Ketenes: An Approach to trans-gamma-Lactones'. Journal of Organic Chemistry, 78 :4587-4593 [DOI] [Details]
2012 'Catalytic asymmetric heterodimerization of ketenes'
Ibrahim AA;Nalla D;Van Raaphorst M;Kerrigan NJ; (2012) 'Catalytic asymmetric heterodimerization of ketenes'. Journal of the American Chemical Society, 134 (6) [DOI] [Details]
2012 'BINAPHANE-Catalyzed Asymmetric Synthesis of trans-beta-Lactams from Disubstituted Ketenes and N-Tosyl Arylimines'
Chen, S;Salo, EC;Wheeler, KA;Kerrigan, NJ (2012) 'BINAPHANE-Catalyzed Asymmetric Synthesis of trans-beta-Lactams from Disubstituted Ketenes and N-Tosyl Arylimines'. Organic Letters, 14 :1784-1787 [DOI] [Details]
2010 'Josiphos-catalyzed asymmetric homodimerization of ketoketenes'
Ibrahim AA;Wei PH;Harzmann GD;Kerrigan NJ; (2010) 'Josiphos-catalyzed asymmetric homodimerization of ketoketenes'. Journal of Organic Chemistry, 75 (22) [DOI] [Details]
2010 'Mechanistic studies of the phosphine-catalyzed homodimerization of ketoketenes'
Wei, PH;Ibrahim, AA;Mondal, M;Nalla, D;Harzmann, GD;Tedeschi, FA;Wheeler, KA;Kerrigan, NJ (2010) 'Mechanistic studies of the phosphine-catalyzed homodimerization of ketoketenes'. Tetrahedron Letters, 51 :6690-6694 [DOI] [Details]
2010 'Phosphine-catalyzed asymmetric synthesis of beta-lactones from arylketoketenes and aromatic aldehydes'
Mondal M;Ibrahim AA;Wheeler KA;Kerrigan NJ; (2010) 'Phosphine-catalyzed asymmetric synthesis of beta-lactones from arylketoketenes and aromatic aldehydes'. Organic Letters, 12 (8) [DOI] [Details]
2009 'Organocatalytic dimerization of ketoketenes'
Ibrahim AA;Harzmann GD;Kerrigan NJ; (2009) 'Organocatalytic dimerization of ketoketenes'. Journal of Organic Chemistry, 74 (4) [DOI] [Details]
2009 'Synthesis of 1,3-diketones through ring-opening of ketoketene dimer beta-lactones'
Ibrahim, AA;Smith, SM;Henson, S;Kerrigan, NJ (2009) 'Synthesis of 1,3-diketones through ring-opening of ketoketene dimer beta-lactones'. Tetrahedron Letters, 50 :6919-6922 [DOI] [Details]
2016 'Asymmetric Synthesis of Dipropionate Derivatives through Catalytic Hydrogenation of Enantioenriched E-Ketene Heterodimers'
Chen, S;Mondal, M;Ibrahim, AA;Wheeler, KA;Kerrigan, NJ (2016) 'Asymmetric Synthesis of Dipropionate Derivatives through Catalytic Hydrogenation of Enantioenriched E-Ketene Heterodimers'. Synthesis (Germany), 48 :2619-2626 [DOI] [Details]
2016 'Alkaloid-Catalyzed Enantioselective [3 + 2] Cycloaddition of Ketenes and Azomethine Imines'
Mondal M;Wheeler KA;Kerrigan NJ; (2016) 'Alkaloid-Catalyzed Enantioselective [3 + 2] Cycloaddition of Ketenes and Azomethine Imines'. Organic Letters, 18 (16) [DOI] [Details]
2016 'Catalytic Asymmetric Synthesis of Ketene Heterodimer beta-Lactones: Scope and Limitations'
Chen, S;Ibrahim, AA;Peraino, NJ;Nalla, D;Mondal, M;Van Raaphorst, M;Kerrigan, NJ (2016) 'Catalytic Asymmetric Synthesis of Ketene Heterodimer beta-Lactones: Scope and Limitations'. Journal of Organic Chemistry, 81 :7824-7837 [DOI] [Details]
2015 'Diastereoselective Synthesis of gamma-Lactones through Reaction of Enediolates with alpha,beta-Unsaturated Sulfoxonium Salts'
Peraino, NJ;Wheeler, KA;Kerrigan, NJ (2015) 'Diastereoselective Synthesis of gamma-Lactones through Reaction of Enediolates with alpha,beta-Unsaturated Sulfoxonium Salts'. Organic Letters, 17 :1735-1737 [DOI] [Details]
2015 'Asymmetric Synthesis of Deoxypropionate Derivatives via Catalytic Hydrogenolysis of Enantioenriched Z-Ketene Heterodimers'
Chen S;Ibrahim AA;Mondal M;Magee AJ;Cruz AJ;Wheeler KA;Kerrigan NJ; (2015) 'Asymmetric Synthesis of Deoxypropionate Derivatives via Catalytic Hydrogenolysis of Enantioenriched Z-Ketene Heterodimers'. Organic Letters, 17 (13) [DOI] [Details]

Research Interests

Our group’s research is concerned with the development of efficient enantioselective and diastereoselective synthetic methods, and their application to the synthesis of drug molecules and natural products. We also carry out extensive mechanistic studies of our new reactions, principally through NMR spectroscopy (e.g. 31P NMR and 1H NMR), to gain mechanistic insight, identify intermediates, and establish general patterns of reactivity.  Much of our studies in recent years have involved the development of chiral organic nucleophile-catalyzed synthetic methods.  Specifically, we have developed a number of chiral phosphine-catalyzed reactions of ketenes providing versatile methods for the asymmetric synthesis of biologically important molecules such as β-lactones (ketene dimers and saturated β-lactones) and β-lactams. 

In 2012, we disclosed the first catalytic asymmetric heterodimerization of ketenes. This reaction was catalyzed by an alkaloid nucleophile (a quinine or quinidine derivative) to give a β-lactone ketene heterodimer product. One current avenue of intense research in our lab involves elaboration of our ketene heterodimer products to cancer therapeutic agents and complex molecules isolated from mycobacterium tuberculosis.  We also have an interest in sulfur and phosphorus chemistry, as well as the development of new transition metal-catalyzed cross-coupling reactions.  In the area of sulfoxonium ylide chemistry, we published a modification of the Johnson-Corey-Chaykovsky reaction which facilitated a synthesis of gamma-lactones, through interception of a sulfoxonium ylide-derived betaine intermediate by a ketene molecule. This work has more recently led to us to investigate new reactions of vinyl sulfoxonium salts, providing routes to pharmaceutically important cyclic molecules.


Research Projects

  Title Funder From - To Role Award
Catalytic Asymmetric Synthesis of Cyclopentanones and Application to the Synthesis of Prostaglandin Pharmaceuticals [Shubhanjan Mitra] Irish Research Council 01-OCT-19 - 30-SEP-21 DCU PI 91,850.10
Catalytic Asymmetric Synthesis of Cyclopentanones and Application to the Synthesis of Prostaglandin Pharmaceuticals. Science Foundation Ireland 01-OCT-19 - 30-SEP-20 DCU PI 68,500.99
Asymmetric Synthesis of gamma-Lactones from Sulfoxonium Salts. National Science Foundation (USA) 01-SEP-15 - 31-AUG-18 Principle Investigator 267,661.00