Synlett 2017; 28(11): 1244-1249
DOI: 10.1055/s-0036-1588754
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3,3-Dialkylated Oxindoles by Oxidative Radical 1,2-Alkylarylation of α,β-Unsaturated Amides

Promita Biswas
Department of Organic Chemistry, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India   Email: ocjg@iacs.res.in
,
Subhasis Paul
Department of Organic Chemistry, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India   Email: ocjg@iacs.res.in
,
Joyram Guin*
Department of Organic Chemistry, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, India   Email: ocjg@iacs.res.in
› Author Affiliations
Further Information

Publication History

Received: 09 January 2017

Accepted after revision: 24 February 2017

Publication Date:
21 March 2017 (online)

Abstract

3,3-Dialkylated oxindoles (1,3-dihydro-2H-indol-2-ones), particularly those containing C3 quaternary stereogenic centers, occupy an important place in organic synthesis and drug discovery. The radical 1,2-alkylarylation of activated olefins with alkyl radicals has emerged as the most atom- and step-economical approach to 3,3-dialkylated oxindoles. This article covers important developments in the area of oxidative radical alkylation/cyclization cascade reactions of α,β-unsaturated amides toward the synthesis of alkyl-substituted oxindoles by employing a range of alkyl-radical precursors and various reaction conditions.

 
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