Memory of chirality in cascade rearrangements of enediynes.

Malek Nechab, Damien Campolo, Julien Maury, Patricia Perfetti, Nicolas Vanthuyne, Didier Siri, Michèle P Bertrand

Laboratoire Chimie Provence, LCP UMR 6264, Aix-Marseille Université, Faculté des Sciences St Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France. malek.nechab@univ-provence.fr

Journal of the American Chemical Society 2010 Oct 27

filter terms:

The cascade rearrangement of chiral enediynes 1c-e, involving successively 1,3-proton shift, Saito-Myers cyclization, 1,5-hydrogen atom transfer, and intramolecular coupling of the resulting biradical, proceeded at 80 °C to form tri- and tetracyclic heterocycles possessing a quaternary stereogenic center with a very high level of memory of chirality.

Citation

Malek Nechab, Damien Campolo, Julien Maury, Patricia Perfetti, Nicolas Vanthuyne, Didier Siri, Michèle P Bertrand. Memory of chirality in cascade rearrangements of enediynes. Journal of the American Chemical Society. 2010 Oct 27;132(42):14742-4