title: Tröger's base twisted amides: endo functionalization and synthesis of an inverted crown ether.
abstract: Taking advantage of the unconventional reactivity of twisted mono- and bis-amides of Tröger's base (TB), rac-6 and rac-7, respectively, the first synthesis of a 6-endo-monosubstituted TB analogue, rac-9, and the first rational synthesis of a 6,12-endo,endo-disubstituted TB analogue, rac-11, have been achieved. The bis-TB crown ether, meso-13, was prepared starting from rac-7. Meso-13 constitutes a rare example of a crown ether with an inverted methylene bridge-to-bridge bis-TB conformation both in solution and in the solid state, resulting in a reluctance to act as a receptor for cations.
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University, P.O. Box 124, 22100 Lund, Sweden.
authors.forename: Josep
authors.initials: J
authors.lastname: Artacho
authors.forename: Erhad
authors.initials: E
authors.lastname: Ascic
authors.forename: Toni
authors.initials: T
authors.lastname: Rantanen
authors.forename: Carl-Johan
authors.initials: CJ
authors.lastname: Wallentin
authors.forename: Sami
authors.initials: S
authors.lastname: Dawaigher
authors.forename: Karl-Erik
authors.initials: KE
authors.lastname: Bergquist
authors.forename: Michael
authors.initials: M
authors.lastname: Harmata
authors.forename: Victor
authors.initials: V
authors.lastname: Snieckus
authors.forename: Kenneth
authors.initials: K
authors.lastname: Wärnmark