Highly diastereoselective synthesis of trifluoromethyl indolines by interceptive benzylic decarboxylative cycloaddition of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides under palladium catalysis
A highly diastereoselective synthesis of trifluoromethyl-substituted indolines under palladium catalysis is disclosed. The reaction proceeds by interceptive decarboxylative benzylic cycloaddition (IDBC) of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides. The palladium-π-benzyl zwitteri...
| Main Authors: | , , , |
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| Format: | Journal article |
| Language: | English |
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American Chemical Society
2018
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| _version_ | 1797105416625192960 |
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| author | Punna, N Das, P Gouverneur, V Shibata, N |
| author_facet | Punna, N Das, P Gouverneur, V Shibata, N |
| author_sort | Punna, N |
| collection | OXFORD |
| description | A highly diastereoselective synthesis of trifluoromethyl-substituted indolines under palladium catalysis is disclosed. The reaction proceeds by interceptive decarboxylative benzylic cycloaddition (IDBC) of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides. The palladium-π-benzyl zwitterionic intermediates are suggested for this transformation, and this would be the first example of an IDBC reaction. |
| first_indexed | 2024-03-07T06:47:14Z |
| format | Journal article |
| id | oxford-uuid:fb477be4-63eb-458d-9d0e-254b3ebeb8b0 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:47:14Z |
| publishDate | 2018 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:fb477be4-63eb-458d-9d0e-254b3ebeb8b02022-03-27T13:12:36ZHighly diastereoselective synthesis of trifluoromethyl indolines by interceptive benzylic decarboxylative cycloaddition of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides under palladium catalysisJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:fb477be4-63eb-458d-9d0e-254b3ebeb8b0EnglishSymplectic Elements at OxfordAmerican Chemical Society2018Punna, NDas, PGouverneur, VShibata, NA highly diastereoselective synthesis of trifluoromethyl-substituted indolines under palladium catalysis is disclosed. The reaction proceeds by interceptive decarboxylative benzylic cycloaddition (IDBC) of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides. The palladium-π-benzyl zwitterionic intermediates are suggested for this transformation, and this would be the first example of an IDBC reaction. |
| spellingShingle | Punna, N Das, P Gouverneur, V Shibata, N Highly diastereoselective synthesis of trifluoromethyl indolines by interceptive benzylic decarboxylative cycloaddition of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides under palladium catalysis |
| title | Highly diastereoselective synthesis of trifluoromethyl indolines by interceptive benzylic decarboxylative cycloaddition of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides under palladium catalysis |
| title_full | Highly diastereoselective synthesis of trifluoromethyl indolines by interceptive benzylic decarboxylative cycloaddition of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides under palladium catalysis |
| title_fullStr | Highly diastereoselective synthesis of trifluoromethyl indolines by interceptive benzylic decarboxylative cycloaddition of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides under palladium catalysis |
| title_full_unstemmed | Highly diastereoselective synthesis of trifluoromethyl indolines by interceptive benzylic decarboxylative cycloaddition of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides under palladium catalysis |
| title_short | Highly diastereoselective synthesis of trifluoromethyl indolines by interceptive benzylic decarboxylative cycloaddition of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides under palladium catalysis |
| title_sort | highly diastereoselective synthesis of trifluoromethyl indolines by interceptive benzylic decarboxylative cycloaddition of nonvinyl trifluoromethyl benzoxazinanones with sulfur ylides under palladium catalysis |
| work_keys_str_mv | AT punnan highlydiastereoselectivesynthesisoftrifluoromethylindolinesbyinterceptivebenzylicdecarboxylativecycloadditionofnonvinyltrifluoromethylbenzoxazinanoneswithsulfurylidesunderpalladiumcatalysis AT dasp highlydiastereoselectivesynthesisoftrifluoromethylindolinesbyinterceptivebenzylicdecarboxylativecycloadditionofnonvinyltrifluoromethylbenzoxazinanoneswithsulfurylidesunderpalladiumcatalysis AT gouverneurv highlydiastereoselectivesynthesisoftrifluoromethylindolinesbyinterceptivebenzylicdecarboxylativecycloadditionofnonvinyltrifluoromethylbenzoxazinanoneswithsulfurylidesunderpalladiumcatalysis AT shibatan highlydiastereoselectivesynthesisoftrifluoromethylindolinesbyinterceptivebenzylicdecarboxylativecycloadditionofnonvinyltrifluoromethylbenzoxazinanoneswithsulfurylidesunderpalladiumcatalysis |