http://hdl.handle.net/10468/291 Thu, 02 May 2013 02:25:28 GMT 2013-05-02T02:25:28Z http://hdl.handle.net/10468/946 Investigating the influence of the sulfur oxidation state on solid state Daly, Carla A.; Eccles, Kevin S.; Bateman, Lorraine M.; O'Boyle, Noel M.; Lawrence, Simon E.; Maguire, Anita R. Design, synthesis and structural characterization of a series of diphenylacetylene derivatives bearing organosulfur, amide and amine moieties has been achieved in which the molecular conformation is controlled through variation of the hydrogen bond properties on alteration of the oxidisation level of sulfur. Sat, 01 Dec 2012 00:00:00 GMT http://hdl.handle.net/10468/946 2012-12-01T00:00:00Z http://hdl.handle.net/10468/609 Recent trends in whole cell and isolated enzymes in enantioselective synthesis Milner, Sinéad E.; Maguire, Anita R. Modern synthetic organic chemistry has experienced an enormous growth in biocatalytic methodologies; enzymatic transformations and whole cell bioconversions have become generally accepted synthetic tools for asymmetric synthesis. This review details an overview of the latest achievements in biocatalytic methodologies for the synthesis of enantiopure compounds with a particular focus on chemoenzymatic synthesis in non-aqueous media, immobilisation technology and dynamic kinetic resolution. Furthermore, recent advances in ketoreductase technology and their applications are also presented. Sun, 20 May 2012 00:00:00 GMT http://hdl.handle.net/10468/609 2012-05-20T00:00:00Z http://hdl.handle.net/10468/920 Utilizing sulfoxide···iodine halogen bonding for cocrystallization Eccles, Kevin S.; Morrison, Robin; Stokes, Stephen P.; O'Mahony, Graham E.; Hayes, John; Kelly, Dawn M.; O'Boyle, Noel M.; Fábián, László; Moynihan, Humphrey A.; Maguire, Anita R.; Lawrence, Simon E. The propensity of a range of different sulfoxides and sulfones to cocrystallize with either 1,2- or 1,4-diiodotetrafluorobenzene, via I•••O=S halogen bonding, was investigated. Cocrystallization occurred exclusively with 1,4-diiodotetrafluorobenzene in either a 1:1 or 1:2 stoichiometry of the organohalide and the sulfoxide, respectively, depending on the sulfoxide used. It was found that the stoichiometry observed was not necessarily related to whether the oxygen acts as a single halogen bond acceptor or if it is bifurcated; with I•••π interactions observed in two of the cocrystals synthesized. Only those cocrystals with a 1:2 stoichiometry exhibit C−H•••O hydrogen bonding in addition to I•••O=S halogen bonding. Examination of the Cambridge Structural Database shows that (i) the I•••O=S interaction is similar to other I•••O interactions, and (ii) the I•••π interaction is significant, with the distances in the two cocrystals among the shortest known. Tue, 01 May 2012 00:00:00 GMT http://hdl.handle.net/10468/920 2012-05-01T00:00:00Z http://hdl.handle.net/10468/988 Copper-catalyzed asymmetric oxidation of sulfides O'Mahony, Graham E.; Ford, Alan; Maguire, Anita R. Copper-catalyzed asymmetric sulfoxidation of aryl benzyl and aryl alkyl sulfides, using aqueous hydrogen peroxide as the oxidant, has been investigated. A relationship between the steric effects of the sulfide substituents and the enantioselectivity of the oxidation has been observed, with up to 93% ee for 2-naphthylmethyl phenyl sulfoxide, in modest yield in this instance (up to 30%). The influence of variation of solvent and ligand structure was examined, and the optimized conditions were then used to oxidize a number of aryl alkyl and aryl benzyl sulfides, producing sulfoxides in excellent yields in most cases (up to 92%), and good enantiopurities in certain cases (up to 84% ee). Fri, 24 Feb 2012 00:00:00 GMT http://hdl.handle.net/10468/988 2012-02-24T00:00:00Z