- Chemoenzymatic synthesis of chiral 2,2′-bipyridine ligands and their N-oxide derivatives: Applications in the asymmetric aminolysis of epoxides and asymmetric allylation of aldehydes
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A series of enantiopure 2,2′-bipyridines have been synthesised from the corresponding cis-dihydrodiol metabolites of 2-chloroquinolines. Several of the resulting hydroxylated 2,2′-bipyridines were found to be useful chiral ligands for the asymmetric amino
- Boyd,Sharma,Sbircea,Murphy,Malone,James,Allen,Hamilton
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experimental part
p. 1081 - 1090
(2010/06/13)
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- Azaarene cis-dihydrodiol-derived 2,2′-bipyridine ligands for asymmetric allylic oxidation and cyclopropanation
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Biphenyl dioxygenase-catalysed cis-dihydroxylation of 2-chloroquinoline, 2-chloro-3-methylquinoline and 2-chloro-6-phenylpyridine substrates yielded the corresponding enantiopure cis-dihydrodiols; enantiopure 2,2′-bipyridines, synthesised in four steps fr
- Boyd, Derek R.,Sharma, Narain D.,Sbircea, Lenuta,Murphy, Deirdre,Belhocine, Tayeb,Malone, John F.,James, Stuart L.,Allen, Christopher C. R.,Hamilton, John T. G.
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supporting information; experimental part
p. 5535 - 5537
(2009/04/12)
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- Dioxygenase-catalyzed cis-dihydroxylation of pyridine-ring systems
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Toluene dioxygenase-catalyzed dihydroxylation, in the carbocyclic rings of quinoline, 2-chloroquinoline, 2-methoxyquinoline, and 3-bromoquinoline, was found to yield the corresponding enantiopure cis-5,6- and -7,8-dihydrodiol metabolites using whole cells
- Boyd, Derek R.,Sharma, Narain D.,Modyanova, Ludmila V.,Carroll, Jonathan G.,Malone, John F.,Allen, Christopher C.R.,Hamilton, John T.G.,Gibson, David T.,Parales, Rebecca E.,Dalton, Howard
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p. 589 - 600
(2007/10/03)
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- Dioxygenase-catalysed cis-dihydrodiol formation in the carbo- and hetero-cyclic rings of quinolines
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Evidence of enzyme-catalysed cis-dihydroxylation in the pyridine (3,4-bond) and benzene rings (5,6- and 7,8-bonds) of quinoline and 2-substituted quinolines is examined in light of the isolation of a heterocyclic cis-diol derivative of 2-quinolone, as a single enantiomer of opposite absolute configuration to that found for the enantiopure carbocyclic cis-diol metabolites from quinolines.
- Boyd,Sharma,Carroll,Malone,Mackerracher,Allen
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p. 683 - 684
(2007/10/03)
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