Asymmetric synthesis of [7]helicene-like molecules

Irena G Stará; Zuzana Alexandrová; Filip Teplý; Petr Sehnal; Ivo Starý; David Saman; Milos Budesínský; Josef Cvacka

doi:10.1021/ol047311p

Asymmetric synthesis of [7]helicene-like molecules

Org Lett. 2005 Jun 23;7(13):2547-50. doi: 10.1021/ol047311p.

Authors

Irena G Stará¹, Zuzana Alexandrová, Filip Teplý, Petr Sehnal, Ivo Starý, David Saman, Milos Budesínský, Josef Cvacka

Affiliation

¹ Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic. stara@uochb.cas.cz

PMID: 15957887
DOI: 10.1021/ol047311p

Abstract

[reaction: see text] A new approach to nonracemic [7]helicene-like molecules has been developed. Stereoselective Co(I)-mediated [2 + 2 + 2] cycloisomerization of aromatic triynes containing an asymmetric carbon atom produces [7]helicene-like scaffolds in diastereomeric ratios up to 100:0. This central-to-helical chirality transfer can be controlled by the absolute configuration at the asymmetric center and by the presence of carbon substituents.