Chromophoric binaphthyl derivatives

Org Lett. 2005 Aug 18;7(17):3661-4. doi: 10.1021/ol051139n.

Abstract

A short synthetic route is outlined, starting from bromo-BN derivatives, via halogen lithium exchange, subsequent Michael reaction with dimethylaminoacrolein, hydrolysis to the corresponding aldehyde, and final condensation with a benzothiazolium unit to produce a BN-pentamethinium system, which absorbs in the visible range around 450 nm. Enantiopure ligands show a decent Cotton effect in the CD spectrum. Preliminary data show potential of these compounds in the area of supramolecular chemistry (enantioselective recognition) and also for medicinal application (induction of apoptosis). [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Apoptosis / drug effects
  • Catalysis
  • Circular Dichroism
  • Hydrocarbons, Brominated / chemistry*
  • Molecular Structure
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / chemistry*
  • Stereoisomerism

Substances

  • Hydrocarbons, Brominated
  • Naphthalenes