Synthesis of chiral [5]helicenes using aromatic oxy-Cope rearrangement as a key step

Both enantiomers of ( P)-(+)-2- and ( M)-(−)-2-acetoxy-11,14-dimethyl[5]helicenes 8 were synthesized by asymmetric aromatic oxy-Cope rearrangement of the corresponding chiral bridged bicyclic compounds, which were obtained by enzymatic resolution. The absolute configurations of 8 were assigned by th...

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Published inTetrahedron letters Vol. 44; no. 10; pp. 2167 - 2170
Main Authors Ogawa, Yasushi, Toyama, Masahito, Karikomi, Michinori, Seki, Katsura, Haga, Kazuo, Uyehara, Tadao
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 03.03.2003
Elsevier
Subjects
aromatic oxy-Cope rearrangement
bicyclic compounds
Chemistry
Chemistry, Organic
chiral helicenes
Physical Sciences
Science & Technology
bicyclic compounds
aromatic oxy-Cope rearrangement
chiral helicenes
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Summary:Both enantiomers of ( P)-(+)-2- and ( M)-(−)-2-acetoxy-11,14-dimethyl[5]helicenes 8 were synthesized by asymmetric aromatic oxy-Cope rearrangement of the corresponding chiral bridged bicyclic compounds, which were obtained by enzymatic resolution. The absolute configurations of 8 were assigned by their circular dichroism spectra. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(03)00150-3