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Synthesis of lactams by isomerization of oxindoles substituted at C-3 by an ω-amino chain.

Abstract : Oxindoles substituted at N-1 by electron-withdrawing groups and at C-3 by ω-amino chains of various lengths undergo mild and easy isomerization to new 5- to 12-membered lactams in good yields (30-96%). As efficient asymmetric syntheses of diversely 3,3-disubstituted oxindoles are currently developed, this isomerization provides a new and valuable access to medium-sized lactams α-substituted with a quaternary asymmetric carbon bearing a 2-aminophenyl residue.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01114417
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Submitted on : Monday, February 9, 2015 - 1:52:36 PM
Last modification on : Thursday, March 5, 2020 - 2:05:19 PM

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Daad Sarraf, Nicolas Richy, Joëlle Vidal. Synthesis of lactams by isomerization of oxindoles substituted at C-3 by an ω-amino chain.. Journal of Organic Chemistry, American Chemical Society, 2014, 79 (22), pp.10945-55. ⟨10.1021/jo501978j⟩. ⟨hal-01114417⟩

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