Azaarene cis-dihydrodiol-derived 2,2'-bipyridine ligands for asymmetric allylic oxidation and cyclopropanation.
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 from 2-chloroquinoline, proved to be efficient chiral ligands in catalytic asymmetric allylic oxidation and cyclopropanation reactions of alkenes.
Boyd
Derek R
DR
Centre for the Theory and Application of Catalysis, Queen's University Belfast, Belfast, UKBT9 5AG. dr.boyd@qub.ac.uk
Sharma
Narain D
ND
Sbircea
Lenuta
L
Murphy
Deirdre
D
Belhocine
Tayeb
T
Malone
John F
JF
James
Stuart L
SL
Allen
Christopher C R
CC
Hamilton
John T G
JT
D015082:2,2'-Dipyridyl / Q000138:chemical synthesis / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D049308:Dioxygenases / Q000737:chemistry; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000475:Alkenes; D000498:Allyl Compounds; D001372:Aza Compounds; D003521:Cyclopropanes; D008024:Ligands; D009281:Naphthalenes; C507866:trans-1,2-dihydro-1,2-naphthalenediol; D015082:2,2'-Dipyridyl; D049308:Dioxygenases