Skeletal rearrangements in the 2,3-diazanorbornene series. A fast access to highly functionalized cyclopentanes.
[reaction: see text] Acid-catalyzed nucleophilic substitution of bicyclic hydrazine-epoxide involves nitrogen participation, leading to a skeletal rearrangement. This transformation enables the fast preparation of disubstituted bicyclic hydrazines in a regio- and stereoselective manner, leading to several polyfunctional diaminocyclopentanes after hydrogenolysis.
Bournaud
Chloée
C
Laboratoire de Chimie Thérapeutique, UMR 8638 associée au CNRS et à l'Université René Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, Paris, France.
Bonin
Martine
M
Micouin
Laurent
L