title: Green asymmetric synthesis: β-amino alcohol-catalyzed direct asymmetric aldol reactions in aqueous micelles.
abstract: The ability of chiral β-amino alcohols to catalyze the direct asymmetric aldol reaction was evaluated for the first time in aqueous micellar media. A family of cheap and easily accessible β-amino alcohols, obtained in one step from naturally occurring amino acids, was shown to successfully catalyze the asymmetric aldol reaction between a series of ketones and aromatic aldehydes. These aldol reactions furnished the corresponding β-hydroxy ketones with up to 93% isolated yield and 89% ee. (S)-2-phenylglycinol and Triton X-100 proved to be the best organocatalyst and surfactant, respectively.
authors.affiliation: Institute of Physical Chemistry, NCSR Demokritos, 15310, Athens, Greece.
authors.forename: Afroditi
authors.initials: A
authors.lastname: Pinaka
authors.forename: Georgios C
authors.initials: GC
authors.lastname: Vougioukalakis
authors.forename: Dimitra
authors.initials: D
authors.lastname: Dimotikali
authors.forename: Elina
authors.initials: E
authors.lastname: Yannakopoulou
authors.forename: Bezhan
authors.initials: B
authors.lastname: Chankvetadze
authors.forename: Kyriakos
authors.initials: K
authors.lastname: Papadopoulos
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D055772:Green Chemistry Technology; D007659:Ketones / Q000737:chemistry*; D008823:Micelles; D014867:Water / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000605:Amino Alcohols; D007659:Ketones; D008823:Micelles; D014867:Water