Elsevier

Tetrahedron Letters

Volume 53, Issue 52, 26 December 2012, Pages 7131-7134
Tetrahedron Letters

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

https://doi.org/10.1016/j.tetlet.2012.10.092Get rights and content

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 amides by a mild two-step sequence.

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Acknowledgments

Financial support for this research from the Uehara Memorial Foundation and the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT, No. 21790026 and 23780115) is gratefully acknowledged. We thank Dr. Kenji Yoza (Bruker AXS) for the X-ray crystallographic analysis.

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