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Highly diastereoselective synthesis of trifluoromethyl indolines by interceptive benzylic decarboxylative cycloaddition of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides under palladium catalysis

Abstract:
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.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/acs.orglett.8b00237

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Merton College
Role:
Author
ORCID:
0000-0001-8638-5308
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Role:
Author
ORCID:
0000-0002-3742-4064
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Name:
Japan Science and Technology Agency
Grant:
JPMJCR12Z7
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Name:
Japan Society for the Promotion of Science
Grant:
KAKENHI
JP 16H01142
Publisher:
American Chemical Society
Journal:
Organic Letters More from this journal
Volume:
20
Issue:
6
Pages:
1526-1529
Publication date:
2018-02-23
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Pmid:
29474077
Language:
English
Pubs id:
pubs:828709
UUID:
uuid:fb477be4-63eb-458d-9d0e-254b3ebeb8b0
Local pid:
pubs:828709
Source identifiers:
828709
Deposit date:
2018-10-03

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