Journal
TETRAHEDRON
Volume 67, Issue 14, Pages 2693-2701Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.01.003
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Funding
- PAPIIT (DGPA, UNAM) [IN204910]
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An efficient and convenient access to 2-tert-butylisoindolin-1-ones via an oxidative radical cyclization process from stable carbamoylxanthates, derived from secondary tert-butylamines, is described. The proposed mechanism for this transformation involves, the generation of a carbamoyl radical, its cyclization to the aromatic system, and the dilauroyl peroxide (DLP) mediated rearomatization to generate the isoindolinone ring system. Additionally, the syntheses of cichorine and 4-hydroxyisoindolin-1-one natural products were carried out to underscore the synthetic potential of this xanthate-based carbamoyl radical-oxidative cyclization. (C) 2011 Elsevier Ltd. All rights reserved.
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