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Diastereoselective Access to trans -2-Substituted Cyclopentylamines

Abstract : A highly diastereoselective synthesis of trans-2-substituted cyclopentylamines via a tandem hydrozirconation/Lewis acid-mediated cyclization sequence applied to butenyl oxazolidines is described. The method allows an easy preparation of diversely substituted cyclopentylamines which appear to be useful synthetic intermediates. This was further illustrated by the syntheses of (±)-Rodocaine, (±)-trans-pentacin, and enantiomerically enriched trans-cyclopentane-1,2-diamine.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02548596
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Submitted on : Monday, April 20, 2020 - 5:43:36 PM
Last modification on : Tuesday, April 21, 2020 - 1:49:57 AM

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Antoine Joosten, Émilie Lambert, Jean-Luc Vasse, Jan Szymoniak. Diastereoselective Access to trans -2-Substituted Cyclopentylamines. Organic Letters, American Chemical Society, 2010, 12 (22), pp.5128-5131. ⟨10.1021/ol102038x⟩. ⟨hal-02548596⟩

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