Stereoselective ring opening of meso bicyclic hydrazines: a straightforward approach to hydrazino cyclopentenic cores.
The diastereoselective synthesis of hydrazinocyclopentenes 6 or 7 can be achieved in a straightforward manner from Diels-Alder adduct 4 using an acid-catalyzed rearrangement or a palladium-catalyzed allylic substitution reaction. In the latter case, enantioenriched compounds with ee values up to 58% can be obtained when an appropriate chiral ligand is used. [reaction: see text]
Luna
Alejandro Pérez
AP
Laboratoire de Chimie Thérapeutique, UMR 8638 Associée au CNRS et à l'Université René Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4 av de l'Observatoire, 75270 Paris Cedex 06, France.
Cesario
Michèle
M
Bonin
Martine
M
Micouin
Laurent
L