title: Enantiomerically pure bithiophene diphosphine oxides as catalysts for direct double aldol reactions.
abstract: The direct aldol reaction between aryl methyl ketones with aromatic aldehydes in the presence of tetrachlorosilane and a catalytic amount of a chiral bithiophene diphosphine oxide was studied; the product of double aldol addition was isolated as diacetate in good diastereoselectivity (up to 95:5) and enantioselectivities up to 91%. The reaction with heteroaromatic aldehydes was also investigated leading to the corresponding 1,3 diols, in some cases with excellent stereoselectivities.
authors.forename: Andrea
authors.initials: A
authors.lastname: Genoni
authors.forename: Maurizio
authors.initials: M
authors.lastname: Benaglia
authors.forename: Sergio
authors.initials: S
authors.lastname: Rossi
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Celentano
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D009284:Naphthols / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D017655:Silicon Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; C406944:BINOL, naphthol; D002712:Chlorides; D009284:Naphthols; D010087:Oxides; D010720:Phosphines; D017655:Silicon Compounds; C116609:3-hydroxybutanal; C039676:silicon tetrachloride