ENANTIOSELECTIVE [2+2+2] CYCLOISOMERISATION OF ALKYNES IN THE SYNTHESIS OF HELICENES: THE SEARCH FOR EFFECTIVE CHIRAL LIGANDS.

Autor: Stará, Irena G., Andronova, Angelina, kollárovič, Adrian, Vyskočil, Štěpán, Jugé, Sylvain, Lloyd-Jones, Guy C., Guirye, Patrick J., Starý, Ivo
Předmět:
Zdroj: Collection of Czechoslovak Chemical Communications; 2011, Vol. 76 Issue 12, p2005-2022, 18p, 3 Diagrams, 4 Charts
Abstrakt: The enantioselective [2+2+2] cycloisomerisation of the aromatic triynes under nickel(0) catalysis to afford nonracemic [6]- and [7]helicene derivatives has been systematically studied. A collection of mono- and bidentate phosphines, phosphites, phosphinites and phosphinous amides possessing stereogenic units such as chiral centre, axis or plane (or their combinations) has been tested and axially chiral binaphthyl-derived monodentate MOP-type phosphine ligands were the optimal class of ligands. Nickel complexes of these ligands afforded nonracemic tetrahydro[6]helicene in up to 64% ee in a model reaction. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index