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 effic...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2008-11 (43), p.5535-5537
Main Authors: 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
Format: Article
Language:English
Subjects:
2,2'-Dipyridyl - chemical synthesis
2,2'-Dipyridyl - chemistry
Alkenes - chemistry
Allyl Compounds - chemical synthesis
Allyl Compounds - chemistry
Aza Compounds - chemical synthesis
Aza Compounds - chemistry
Catalysis
Crystallography, X-Ray
Cyclization
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
Dioxygenases - chemistry
Ligands
Models, Molecular
Molecular Structure
Naphthalenes - chemical synthesis
Naphthalenes - chemistry
Oxidation-Reduction
Stereoisomerism
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Summary: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.
ISSN:1359-7345
DOI:10.1039/b814678k