title: Diastereodivergent Access to Syn and Anti 3,4-Substituted β-Fluoropyrrolidines: Enhancing or Reversing Substrate Preference.
abstract: A practical diastereodivergent access to β-fluoropyrrolidines with two adjacent stereocenters has been demonstrated, by either enhancing or completely reversing the substrate control, in the diastereoselective fluorination of a series of diverse pyrrolidinyl carbaldehydes using organocatalysis. Furthermore, enamine catalysis has been successfully utilized for kinetic resolution, obtaining a fluorinated β-prolinol analogue with two adjacent tetrasubstituted chiral centers in 95% ee from a racemic substrate.
authors.affiliation: Discovery Chemistry and DMPK, H. Lundbeck A/S, Ottiliavej 9, 2500 Valby, Denmark.|Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen , Universitetsparken 2, 2100 Copenhagen, Denmark.
authors.forename: Kasper
authors.initials: K
authors.lastname: Fjelbye
authors.affiliation: Discovery Chemistry and DMPK, H. Lundbeck A/S, Ottiliavej 9, 2500 Valby, Denmark.
authors.forename: Mauro
authors.initials: M
authors.lastname: Marigo
authors.affiliation: Department of Drug Design and Pharmacology, Faculty of Health and Medical Sciences, University of Copenhagen , Universitetsparken 2, 2100 Copenhagen, Denmark.
authors.forename: Rasmus Prætorius
authors.initials: RP
authors.lastname: Clausen
authors.affiliation: Discovery Chemistry and DMPK, H. Lundbeck A/S, Ottiliavej 9, 2500 Valby, Denmark.
authors.forename: Karsten
authors.initials: K
authors.lastname: Juhl