Skeletal rearrangements in the 2,3-diazanorbornene series. A fast access to highly functionalized cyclopentanes |
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| Authors: | Bournaud Chloée Bonin Martine Micouin Laurent |
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| Affiliation: | Laboratoire de Chimie Thérapeutique, UMR 8638 associée au CNRS et à l'Université René Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, Paris, France. |
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| Abstract: | [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. |
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