Enantioselective synthesis of (-)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction.
The highly enantio- and diastereoselective aldol reaction of isocyanoacetates catalysed by Ag2O and cinchona-derived amino phosphines applied to the synthesis of (-)- and (+)-chloramphenicol is described. The concise synthesis showcases the utility of this catalytic asymmetric methodology for the preparation of bioactive compounds possessing α-amino-β-hydroxy motifs.
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK. darren.dixon@chem.ox.ac.uk.
Allegra
A
Franchino
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK. darren.dixon@chem.ox.ac.uk.
Pavol
P
Jakubec
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK. darren.dixon@chem.ox.ac.uk.
Darren J
DJ
Dixon
D000085:Acetates / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D002701:Chloramphenicol / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
D000085:Acetates; D000447:Aldehydes; D012834:Silver; D002701:Chloramphenicol; C116609:3-hydroxybutanal; C007170:cyanoacetic acid