New Chiral Molecular Tweezers with a Bis-Tröger's Base Skeleton†

Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, E-28040 Madrid, Spain.
The Journal of Organic Chemistry (Impact Factor: 4.56). 02/2001; DOI: 10.1021/jo0010882

ABSTRACT A convenient synthesis of 5α,8α,14α,17α-5,17:8,14-dimethano-5,8,14,17-tetraaza-5,6,7,8,13,14,17,18-octahydrodibenzo[e,e‘]benzo[1,2-a:3,4-a‘]dicyclooctene derivatives is described, and the compounds have been fully characterized by NMR; in some cases, the molecular structure has been determined by X-ray crystallography. These compounds represent the first examples of a new class of molecular tweezers.

  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: 4,6-Bis(bromomethyl)- N <sup>1</sup>, N <sup>3</sup>-bis( tert -butoxycarbonyl)benzene-1,3-diamine is introduced as a general starting compound for the preparation of bis-Tröger's base (bisTB) derivatives in excellent yield in just two steps. The synthetic sequence includes treatment of the above-mentioned protected diamine with an arylamine followed by in situ deprotection and the final bisTB-forming reaction. This sequence allows synthesis of bisTB derivatives, which are not accessible by known procedures. The described approach is a general new method for the preparation of bisTB derivatives from "troegerable" arylamines.
  • [Show abstract] [Hide abstract]
    ABSTRACT: Synthetic strategy for novel multiple Tröger's base derivatives is presented. Compounds were prepared in three steps: o -nitrobenzoylation of benzene-1,2- and -1,3-diamines 3 followed by reduction of nitro and amide groups to amino functions and treatment of the obtained tetraamine compounds 6 with formaldehyde lead to simultaneous formation of bis-Tröger's base (bisTB) derivatives 7a , 7b . Only products of 1,2,3,4-substituted regioisomers with anti conformation were separated from reaction mixtures. The same synthetic procedure was used for preparation of tris-Tröger's base (trisTB) derivative 12b starting from benzene-1,3,5-triamine ( 8 ).
    Collection of Czechoslovak Chemical Communications 01/2002; · 1.00 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: Oligo Tröger's bases are compounds containing two or more Tröger's base subunits (1,5-methanodiareno[b,f][1,5]diazocines) sharing one or more arene parts. Due to their interesting molecular shapes, these compounds are studied as chiral molecular tweezers, clips, cavitands, clefts, calixes, etc. This review includes all available data on oligo Tröger's bases, and introduces their preparation and properties to a wide audience.
    Chemical Society Reviews 03/2012; 41(10):3839-58. · 24.89 Impact Factor