posted on 2014-11-21, 00:00authored byDaad 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.