Synthetic Studies Toward Chiral Aromatic Triynes as Key Substrates for the Asymmetric Synthesis of Helicene-Like Molecules
| Autor: | Filip Teply, David Šaman, Petr Sehnal, Ivo Stary, Irena G. Stará, Zuzana Alexandrová, Pavel Fiedler |
|---|---|
| Rok vydání: | 2004 |
| Předmět: |
Stereochemistry
Enantioselective synthesis Sonogashira coupling chemistry.chemical_element General Medicine General Chemistry chemistry.chemical_compound Cycloisomerization Helicene chemistry Acetylene Computational chemistry Key (cryptography) Organic chemistry Molecule Chirality (chemistry) Palladium |
| Zdroj: | Collection of Czechoslovak Chemical Communications. 69:2193-2211 |
| ISSN: | 1212-6950 0010-0765 |
| DOI: | 10.1135/cccc20042193 |
| Popis: | We have developed the synthesis of model nonracemic aromatic triynes (-)-(S)-1-4 containing the 1-{[2-(but-3-yn-1-yl)-1-naphthyl]ethynyl}-2-{[((S)-1-methylprop-2-yn-1-yl)oxy]- methyl}naphthalene unit. The common 1,2-di(2-substituted-1-naphthyl)acetylene part was constructed via Sonogashira coupling of appropriate 1-iodonaphthalenes with 1-ethynylnaphthalenes both bearing tethered acetylene units in positions 2. The chirality of triynes (-)-(S)-1-4 was introduced by incorporating commercially available (-)-(S)-but-3-yn-2-ol (10) into tethered acetylene units. The nonracemic triynes are intended to be used as substrates in stereoselective [2+2+2] triyne cycloisomerization catalyzed by transition metal complexes. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|