Synthesis of Helicene Scaffolds via [2+2+2] Cycloisomerization of Aromatic Triynes

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Title:Synthesis of Helicene Scaffolds via [2+2+2] Cycloisomerization of Aromatic Triynes
Creators:
Stará, Irena G.
Starý, Ivo
Kollárovič, Adrian
Teplý, Filip
Šaman, David
Fiedler, Pavel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 68, 5, pp. 917-930
Uncontrolled Keywords:Nickel catalysis, Helical chirality, Palladium catalysis, Helicenes, Rhodium catalysis, Triyne cyclotrimerization, Tetrahydrohelicenes, Alkynes, Spiroketals, Cobalt catalysis, Arenes

Abstract

Triynes R-C≡C-CH<sub>2</sub>CH<sub>2</sub>-Ar-C≡C-Ar'-CH<sub>2</sub>CH<sub>2</sub>-C≡C-R were subjected to Co(I)- or Ni(0)-mediated&nbsp;intramolecular [2+2+2] cycloisomerization to provide corresponding tetrahydropentahelicene, tetrahydrohexahelicene, and tetrahydroheptahelicene in good to moderate yields. The reaction tolerates various substituents at pendant acetylene moieties (R = H, CH<sub>3</sub>, trimethylsilyl, not triisopropylsilyl) and fluorine in an aromatic part. By contrast, under Rh(I) or Pd(0) catalysis, triyne with the CH<sub>2</sub>OCH<sub>2</sub> tether lost pendant propargyl moieties and an aromatic spiroketal was formed preferentially. <p>

Title:Synthesis of Helicene Scaffolds via [2+2+2] Cycloisomerization of Aromatic Triynes
Creators:
Stará, Irena G.
Starý, Ivo
Kollárovič, Adrian
Teplý, Filip
Šaman, David
Fiedler, Pavel
Uncontrolled Keywords:Nickel catalysis, Helical chirality, Palladium catalysis, Helicenes, Rhodium catalysis, Triyne cyclotrimerization, Tetrahydrohelicenes, Alkynes, Spiroketals, Cobalt catalysis, Arenes
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:68
Number:5
Page Range:pp. 917-930
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20030917UNSPECIFIED
ID Code:2094
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:15

Citation

Stará, Irena G.; Starý, Ivo; Kollárovič, Adrian; Teplý, Filip; Šaman, David; Fiedler, Pavel (2003) Synthesis of Helicene Scaffolds via [2+2+2] Cycloisomerization of Aromatic Triynes. Collection of Czechoslovak Chemical Communications, 68 (5). pp. 917-930. ISSN 0010-0765

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