title: Dipeptide-catalyzed asymmetric aldol condensation of acetone with (N-alkylated) isatins.
abstract: [reaction: see text] The aldol condensation of acetone with several isatins is described. The desired compound was obtained in quantitative yield and with good enantioselectivities up to 77%. The best results were obtained with 10 mol % H-D-Pro-L-beta3-hPhg-OBn as a catalyst, resulting in the preferential formation of the (R)-enantiomer. The absolute configuration of the newly formed chiral center has been assigned by an X-ray diffraction study and CD spectra analysis of the molecules.
authors.affiliation: Dipartimento di Chimica G. Ciamician, Alma Mater Studiorum Università di Bologna, Via Selmi 2, 40126 Bologna, Italy.
authors.forename: Gianluigi
authors.initials: G
authors.lastname: Luppi
authors.forename: Pier Giorgio
authors.initials: PG
authors.lastname: Cozzi
authors.forename: Magda
authors.initials: M
authors.lastname: Monari
authors.forename: Bernard
authors.initials: B
authors.lastname: Kaptein
authors.forename: Quirinus B
authors.initials: QB
authors.lastname: Broxterman
authors.forename: Claudia
authors.initials: C
authors.lastname: Tomasini