Rhodium-catalyzed decomposition of indole-substituted α-diazo-β-keto esters: three different reactions based on indole oxidation state

Rhodium(II)-catalyzed decomposition of three indole-substituted α-diazo-β-keto esters affords three different types of intramolecular reactions based on the oxidation state of the indole. Treatment of the α-diazo-β-keto esters 8abc with Rh(II) afforded three different reaction products depending on...

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Bibliographic Details
Published in:Tetrahedron letters 2001-09, Vol.42 (39), p.6835-6838
Main Authors: Jung, Michael E, Slowinski, Franck
Format: Article
Language:English
Subjects:
cyclopropanation of indole double bond
oxidation of indoline to indole using carbenoid
oxindole reaction with carbenoids
Rhodium(II)-catalyzed reactions of diazo esters
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Summary:Rhodium(II)-catalyzed decomposition of three indole-substituted α-diazo-β-keto esters affords three different types of intramolecular reactions based on the oxidation state of the indole. Treatment of the α-diazo-β-keto esters 8abc with Rh(II) afforded three different reaction products depending on the oxidation state of the indole, with the indole 8a giving 13 and 14 , the oxindole giving 15 and 16 , and the indoline giving the indole-β-keto ester 17 .
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)01431-9