Memory of chirality in cascade rearrangements of enediynes.
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.
Nechab
Malek
M
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
Campolo
Damien
D
Maury
Julien
J
Perfetti
Patricia
P
Vanthuyne
Nicolas
N
Siri
Didier
D
Bertrand
Michèle P
MP
D003500:Cyclization; D053281:Enediynes / Q000737:chemistry*; D008958:Models, Molecular; D013237:Stereoisomerism
D053281:Enediynes