Tetrahedron Letters

Diastereoselective synthesis of 3, 3-disubstituted oxindoles from atropisomeric N-aryl oxindole derivatives

A Nakazaki, A Mori, S Kobayashi, T Nishikawa

Index: Nakazaki, Atsuo; Mori, Ayako; Kobayashi, Susumu; Nishikawa, Toshio Tetrahedron Letters, 2012 , vol. 53, # 52 p. 7131 - 7134

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Citation Number: 14

Abstract

Diastereoselective synthesis of 3, 3-disubstituted oxindoles has been examined by transformations involving nucleophilic addition, alkylation, and cycloaddition using chiral racemic N-aryl oxindoles bearing C–N axial chirality. The most striking features of this approach are high diastereoselectivities (up to> 95:< 5) when using ortho-monosubstituted N-aryl oxindoles and easy removal of the p-(benzyloxy) aryl moiety in the axially twisted ...