Lewis acid-catalyzed cascade radical addition/cyclization for the synthesis of 3-substituted isoindolin-1-one derivatives

Lianjin Zhang, Jin Bum Kim, Doo Ok Jang

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12 Citations (Scopus)

Abstract

Radical addition reactions to 2-formylbenzoate-derived hydrazones in the presence of a Lewis acid were developed. Under the reaction conditions, the resulting products were readily converted into 3-substituted isoindolin-1-one derivatives. Diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives was also established employing L-proline as a chiral auxiliary. The cascade radical addition-cyclization reaction allows direct access to 3-substituted isoindolin-1-one derivatives under tin-free conditions.

Original languageEnglish
Pages (from-to)2654-2658
Number of pages5
JournalTetrahedron Letters
Volume55
Issue number16
DOIs
Publication statusPublished - 2014 Apr 16

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea ( NRF-2011-0021279 ).

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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