C(2)-symmetric Sc(III)-complexes as chiral Lewis acids. Catalytic enantioselective aldol additions to glyoxylate esters.
Cationic Lewis acid complexes [Sc(pyridyl-bis(oxazolinyl)](Cl(2))SbF(6) 1a and 1b catalyze aldol reactions with ethyl glyoxylate with enantioselectivities ranging from 90 to 99% ee and syn reaction diastereoselections ranging from 90:10 to 95:5. [reaction: see text]
D000147:Acids, Heterocyclic / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D002412:Cations / Q000737:chemistry; D004952:Esters / Q000737:chemistry*; D006038:Glyoxylates / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism
D000147:Acids, Heterocyclic; D000447:Aldehydes; D002412:Cations; D004952:Esters; D006038:Glyoxylates; C116609:3-hydroxybutanal; D012538:Scandium