A long-range chiral relay via tertiary amide group in asymmetric catalysis: new amino acid-derived N,P-ligands for copper-catalysed conjugate addition.
New N,P-ligands 4-6, derived from valinol and prolinol, respectively, have been developed for the asymmetric, copper(I)-catalysed conjugate addition of diethylzinc to unsaturated ketones; the tertiary amide group has been shown to effectively relay the chiral information from the ligand backbone to the active centre.
Malkov
Andrei V
AV
Department of Chemistry, University of Glasgow, Glasgow, UK G12 8QQ. amalkov@chem.gla.ac.uk
Hand
John B
JB
Kocovský
Pavel
P
D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D003300:Copper / Q000737:chemistry*; D008024:Ligands; D008956:Models, Chemical; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism; D014633:Valine / Q000031:analogs & derivatives* / Q000737:chemistry
D000577:Amides; D000596:Amino Acids; D008024:Ligands; D009942:Organometallic Compounds; D011759:Pyrrolidines; C040994:valinol; C010509:prolinol; D003300:Copper; D014633:Valine