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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.
Boyd, D R; Sharma, N D; Sbircea, L; Murphy, D; Malone, J F; James, S L; Allen, C C R; Hamilton, J T G.
Affiliation
  • Boyd DR; School of Chemistry and Chemical Engineering, The Queen's University of Belfast, Belfast, UK BT9 5AG. dr.boyd@qub.ac.uk
Org Biomol Chem ; 8(5): 1081-90, 2010 Mar 07.
Article in En | MEDLINE | ID: mdl-20165798
ABSTRACT
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 aminolysis of meso-epoxides leading to the formation of enantioenriched amino alcohols (-->84% ee). N-oxide and N,N'-dioxide derivatives of these 2,2'-bipyridines, including separable atropisomers, have been synthesised and used as enantioselective organocatalysts in the asymmetric allylation of aldehydes to give allylic alcohols (-->86% ee).
Subject(s)

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Oxides / Quinolines / 2,2'-Dipyridyl Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2010 Document type: Article

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Oxides / Quinolines / 2,2'-Dipyridyl Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2010 Document type: Article