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.
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).
Boyd
D R
DR
School of Chemistry and Chemical Engineering, The Queen's University of Belfast, Belfast, UK BT9 5AG. dr.boyd@qub.ac.uk
Sharma
N D
ND
Sbircea
L
L
Murphy
D
D
Malone
J F
JF
James
S L
SL
Allen
C C R
CC
Hamilton
J T G
JT
D015082:2,2'-Dipyridyl / Q000138:chemical synthesis / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D001711:Biotransformation; D004852:Epoxy Compounds / Q000737:chemistry; D008024:Ligands; D010087:Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D016958:Pseudomonas putida / Q000201:enzymology; D011804:Quinolines / Q000378:metabolism*; D020578:Sphingomonas / Q000201:enzymology
D000447:Aldehydes; D004852:Epoxy Compounds; D008024:Ligands; D010087:Oxides; D011804:Quinolines; D015082:2,2'-Dipyridyl; C083774:2-chloroquinoline