Collect. Czech. Chem. Commun.
2007, 72, 1499-1522
https://doi.org/10.1135/cccc20071499
Synthesis of Methoxy Substituted Centrally Chiral Triynes as Precursors of Functionalised Nonracemic Helicene-Like Compounds
Zuzana Krausováa,b, Petr Sehnalb, Filip Teplýa, Irena G. Staráa,b,*, Ivo Starýa,b,*, David Šamana, Josef Cvačkaa and Pavel Fiedlera
a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
b Center for Biomolecules and Complex Molecular Systems, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
Abstract
A modular synthesis of a series of methoxy substituted optically pure aromatic triynes (-)-(S)-5-9 and (-)-(R)-10 is presented. It relies on key operations such as substitution of benzylic bromine with an alkoxy group and aryl-alkyne coupling reaction to combine appropriate methoxy substituted benzene/naphthalene building blocks and chiral alkynol synthons such as (-)-(2S)-but-3-yn-2-ol and (-)-(1R)-1-phenylprop-2-yn-1-ol. The triyne molecules comprise a diphenylacetylene, 1-(phenylethynyl)naphthalene or 1,1'-ethyne-1,2-diyldinaphthalene core unit. They are intended to serve as [2+2+2] cyclisation precursors of methoxy substituted nonracemic helicene-like compounds with a penta-, hexa- and heptacyclic helical scaffold.
Keywords: Alkynes; Arenes; Helical chirality; Sonogashira reaction; Cross-coupling; Helical structures; Helicenes; Heterohelicenes.
References: 35 live references.
