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Bournaud C, Bonin M, Micouin L. Skeletal rearrangements in the 2,3-diazanorbornene series. A fast access to highly functionalized cyclopentanes. Org Lett. 2006;8(14):3041-3doi: 10.1021/ol060972x.
Bournaud, C., Bonin, M., & Micouin, L. (2006). Skeletal rearrangements in the 2,3-diazanorbornene series. A fast access to highly functionalized cyclopentanes. Organic letters, 8(14), 3041-3. https://doi.org/10.1021/ol060972x
Bournaud, Chloée, et al. "Skeletal rearrangements in the 2,3-diazanorbornene series. A fast access to highly functionalized cyclopentanes." Organic letters vol. 8,14 (2006): 3041-3. doi: https://doi.org/10.1021/ol060972x
Bournaud C, Bonin M, Micouin L. Skeletal rearrangements in the 2,3-diazanorbornene series. A fast access to highly functionalized cyclopentanes. Org Lett. 2006 Jul 06;8(14):3041-3. doi: 10.1021/ol060972x. PMID: 16805547.
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Org Lett. 2006 Jul 06;8(14):3041-3. doi: 10.1021/ol060972x.

Skeletal rearrangements in the 2,3-diazanorbornene series. A fast access to highly functionalized cyclopentanes.

Organic letters

Chloée Bournaud, Martine Bonin, Laurent Micouin

Affiliations

  1. Laboratoire de Chimie Thérapeutique, UMR 8638 associée au CNRS et à l'Université René Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, Paris, France.

PMID: 16805547 DOI: 10.1021/ol060972x

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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