title: Highly stereoselective aldol reactions of titanium enolates from lactate-derived chiral ketones.
abstract: [reaction: see text] Highly stereoselective titanium-mediated aldol reactions based on lactate-derived ketones are reported. The stereochemical outcome of the process depends on the protecting group (PMB or Bn) and the Lewis acid (i-PrOTiCl(3) or TiCl(4)) used in the enolization step, the corresponding anti-syn or syn-syn aldols being prepared in high yields and with diastereomeric ratios up to 99:1.
authors.affiliation: Departament de Química Orgànica, Universitat de Barcelona, Martí i Franqués 1-11, 08028 Barcelona, Catalonia, Spain.
authors.forename: Joan G
authors.initials: JG
authors.lastname: Solsona
authors.forename: Pedro
authors.initials: P
authors.lastname: Romea
authors.forename: Fèlix
authors.initials: F
authors.lastname: Urpí
authors.forename: Jaume
authors.initials: J
authors.lastname: Vilarrasa
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D007773:Lactates / Q000737:chemistry; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D007659:Ketones; D007773:Lactates; D014025:Titanium