180184-99-0Relevant articles and documents
Investigation of additive effects in enantioselective copper-catalysed C-H insertion and aromatic addition reactions of α-diazocarbonyl compounds
Slattery, Catherine N.,Clarke, Leslie-Ann,O'Neill, Shane,Ring, Aoife,Ford, Alan,Maguire, Anita R.
, p. 765 - 767 (2012)
Significant enhancements in enantioselectivities and reaction efficiencies in asymmetric copper-catalysed C-H insertion and aromatic addition reactions of -diazocarbonyl compounds in the presence of various group I salts are reported. For the first time i
Synthetic and mechanistic aspects on the competition between C-H insertion and hydride transfer in copper-mediated transformations of α-diazo-β- keto sulfones
Slattery, Catherine N.,Ford, Alan,Eccles, Kevin S.,Lawrence, Simon E.,Maguire, Anita R.
, p. 591 - 595 (2014/03/21)
Competition between C-H insertion and hydride transfer is reported for the copper-catalysed reactions of a range of phenyl-substituted α-diazo- β-keto sulfones. Control of chemoselectivity is possible by alteration of the electronic properties of the diazo substrate. The production of enantioenriched cyclopentanones (up to 89% ee), formed via C-H insertion, and alkylidene tetrahydrofurans (up to 43% ee), produced via hydride transfer, is described. The isolation of products derived from hydride transfer provides mechanistic insight into the copper-mediated C-H insertion of α-diazoA?carbonyl compounds. Georg Thieme Verlag Stuttgart New York.
Electronic effects of aryl-substituted bis(oxazoline) ligands on the outcome of asymmetric copper-catalysed C-H insertion and aromatic addition reactions
Slattery, Catherine N.,O'Keeffe, Sarah,Maguire, Anita R.
, p. 1265 - 1275 (2013/11/19)
The effect of the modification of bis(oxazoline) ligands on the outcome of copper-catalysed C-H insertion and aromatic addition reactions is described. In general, these reactions display minimum sensitivity in terms of enantiocontrol to variation of the electronic properties of the aryl moiety of the ligand however, some influence is observed for C-H insertions employing naphthyl-substituted bis(oxazolines) and for aromatic addition reactions of biphenyl diazo ketone substrates. The synthesis of the modified bis(oxazolines), which include four novel structures, is also described.
Catalyst, additive and counterion effects on the efficiency and enantioselectivity of copper-catalysed C-H insertion reactions of α-diazosulfones
Slattery, Catherine N.,Clarke, Leslie-Ann,Ford, Alan,Maguire, Anita R.
, p. 1297 - 1301 (2013/02/23)
Asymmetric copper-catalysed intramolecular C-H insertion reactions of α-diazosulfones in the presence of various group I salts are reported leading to substantial variation in reaction efficiencies and enantioselectivities. The borate additives NaBARF and
Asymmetric copper-catalysed intramolecular C-H insertion reactions of α-diazo-β-keto sulfones
Slattery, Catherine N.,Maguire, Anita R.
supporting information; experimental part, p. 667 - 669 (2011/03/20)
Asymmetric copper-catalysed intramolecular C-H insertion reactions of a series of α-diazo-β-keto sulfones are reported. Enantioselectivities of up to 82% ee were achieved in moderate to good yield. These results represent the highest level of enantiocontr
Enantioselective introduction of a benzenesulfonylmethyl substituent at an unactivated carbon atom via chemoenzymatic methods
Maguire, Anita R.,Kelleher, Leonard L.
, p. 7459 - 7462 (2007/10/03)
Introduction of a benzenesulfonylmethyl group at the unactivated γ-carbon of carboxylic acid derivatives has been achieved through a combination of rhodium acetate catalysed carbenoid C-H insertion and baker's yeast mediated kinetic resolution. Access to
