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

Full Text: HTML

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 ...

Related Articles:

Catalyst-free synthesis of 3-hydroxy-3-(alkyl/aryl) indolin-2-ones by addition of organoaluminum reagents to isatins

[Kumar, G. Santosh; Ramesh, Palakuri; Kumar, A. Sanjeeva; Swetha; Meshram Tetrahedron Letters, 2013 , vol. 54, # 37 p. 5048 - 5051]

CeCl 3· 7H 2 O/IBX-promoted oxidation of 3-alkylindoles to 3-hydroxyoxindoles

[Yadav; Reddy, B.V. Subba; Reddy, Ch. Suresh; Krishna Tetrahedron Letters, 2007 , vol. 48, # 11 p. 2029 - 2032]

A novel biotransformation of benzofurans and related compounds catalysed by a chloroperoxidase

[Alvarez, Ricardo G.; Hunter, Iain S.; Suckling, Colin J.; Thomas, Michael; Vitinius, Ute Tetrahedron, 2001 , vol. 57, # 40 p. 8581 - 8587]

More Articles...