Modified Synthesis of Heptahelicene and Its Resolution Into Single Enantiomers

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Title:Modified Synthesis of Heptahelicene and Its Resolution Into Single Enantiomers
Creators:
Alexandrová, Zuzana
Sehnal, Petr
Stará, Irena G.
Starý, Ivo
Šaman, David
Urquhart, Stephen G.
Otero, Edwige
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 71, 8, pp. 1256-1264
Uncontrolled Keywords:Racemate resolution, Cobalt catalysis, Chiral HPLC, Nickel catalysis, Helicenes, Heptahelicene, Alkynes, Enantioselective catalysis, Cycliosomerization, Triynes

Abstract

A practical synthesis of racemic heptahelicene has been develeped being based on key [2+2+2] cycloisomerization of bis[2-(but-3-yn-1-yl)-1-naphthyl]acetylene under CpCo(CO)<sub>2</sub>/PPh<sub>3</sub> or CpCo(C<sub>2</sub>H<sub>4</sub>)<sub>2</sub> catalysis. The application of the Ni(cod)<sub>2</sub> catalyst with (-)-(<i>S</i><sub>a</sub>)-(2'-methoxy-1,1'-binaphthalen-2-yl)diphenylphosphane resulted in enantioselective triyne cyclization to provide (+)-7,8,11,12-tetrahydroheptahelicene in 40% ee. Optically pure (-)-(<i>M</i>)- and optically highly enriched (+)-(<i>P</i>)-heptahelicene were obtained on a milligram scale by resolution of racemate by chiral HPLC on a semipreparative Whelk-O1 column. <p>

Title:Modified Synthesis of Heptahelicene and Its Resolution Into Single Enantiomers
Creators:
Alexandrová, Zuzana
Sehnal, Petr
Stará, Irena G.
Starý, Ivo
Šaman, David
Urquhart, Stephen G.
Otero, Edwige
Uncontrolled Keywords:Racemate resolution, Cobalt catalysis, Chiral HPLC, Nickel catalysis, Helicenes, Heptahelicene, Alkynes, Enantioselective catalysis, Cycliosomerization, Triynes
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:71
Number:8
Page Range:pp. 1256-1264
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20061256UNSPECIFIED
ID Code:2539
Item Type:Article
Deposited On:06 Feb 2009 17:19
Last Modified:06 Feb 2009 16:19

Citation

Alexandrová, Zuzana; Sehnal, Petr; Stará, Irena G.; Starý, Ivo; Šaman, David; Urquhart, Stephen G.; Otero, Edwige (2006) Modified Synthesis of Heptahelicene and Its Resolution Into Single Enantiomers. Collection of Czechoslovak Chemical Communications, 71 (8). pp. 1256-1264. ISSN 0010-0765

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