title: A Protocol for the exo-Mono and exo,exo-Bis Functionalization of the Diazocine Ring of Tröger's Base.
abstract: An efficient protocol has been developed for the exo-mono and exo,exo-bis functionalization of Tröger's base in the benzylic 6 and 12 positions of the diazocine ring. The lithiation of Tröger's base using s-BuLi/TMEDA followed by electrophilic quench affords exo-mono- and exo,exo-bis-substituted derivatives of Tröger's base in good to excellent yields. The variation of the number of equivalents of s-BuLi/TMEDA and the order of addition of the electrophile strongly govern the outcome of the reaction for each electrophile.
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
authors.forename: Sami
authors.initials: S
authors.lastname: Dawaigher
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
authors.forename: Kristoffer
authors.initials: K
authors.lastname: Månsson
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.|Department of Chemistry, Queen's University , Kingston, ON K7L 3N6, Canada.
authors.forename: Erhad
authors.initials: E
authors.lastname: Ascic
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
authors.forename: Josep
authors.initials: J
authors.lastname: Artacho
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
authors.forename: Roger
authors.initials: R
authors.lastname: Mårtensson
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
authors.forename: Nagarajan
authors.initials: N
authors.lastname: Loganathan
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
authors.forename: Ola F
authors.initials: OF
authors.lastname: Wendt
authors.affiliation: Department of Chemistry, University of Missouri-Columbia , Columbia, Missouri 65211, United States.
authors.forename: Michael
authors.initials: M
authors.lastname: Harmata
authors.affiliation: Department of Chemistry, Queen's University , Kingston, ON K7L 3N6, Canada.
authors.forename: Victor
authors.initials: V
authors.lastname: Snieckus
authors.affiliation: Centre for Analysis and Synthesis, Department of Chemistry, Lund University , P.O. Box 124, 221 00 Lund, Sweden.
authors.forename: Kenneth
authors.initials: K
authors.lastname: Wärnmark