American Chemical Society
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Synthesis of Lactams by Isomerization of Oxindoles Substituted at C‑3 by an ω‑Amino Chain

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posted on 2014-11-21, 00:00 authored by Daad Sarraf, Nicolas Richy, Joëlle Vidal
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.