Metal-Free Synthesis of 3,3-Disubstituted Oxoindoles by Iodine(III)-Catalyzed Bromocarbocyclizations

“I” did it: An iodine(III)‐mediated bromocarbocyclization was elaborated as an efficient tool for the synthesis of oxoindoles. This method is applicable to a variety of structurally different substrates, also with chemically sensitive groups, and gives access to the heterocycles in a regio‐ and ster...

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Bibliographic Details
Published in:	Chemistry : a European journal Vol. 18; no. 35; pp. 10834 - 10838
Main Authors:	Fabry, David C., Stodulski, Maciej, Hoerner, Stefanie, Gulder, Tanja
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 27-08-2012 WILEY‐VCH Verlag Wiley Subscription Services, Inc
Subjects:	Acrylamides - chemistry Alkaloids Bromides - chemistry bromocarbocyclization Bromosuccinimide - chemistry Catalysis Chemistry Cyclization Halogenation heterocycles Indoles - chemical synthesis Molecular Structure natural products organocatalysis oxoindoles Physostigmine Physostigmine - chemical synthesis Potassium Compounds - chemistry Substrates Synthesis
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Summary:	“I” did it: An iodine(III)‐mediated bromocarbocyclization was elaborated as an efficient tool for the synthesis of oxoindoles. This method is applicable to a variety of structurally different substrates, also with chemically sensitive groups, and gives access to the heterocycles in a regio‐ and stereoselective fashion (see scheme). The indole‐2‐ones obtained can be converted easily into structurally complex target compounds, such as the alkaloid physostigmine.
Bibliography:	istex:B50E2798EDD2A85F9ABACB2406CD3023C6D5D8A3 ArticleID:CHEM201201232 ark:/67375/WNG-PH9GC5GQ-K Fonds der Chemischen Industrie ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0947-6539 1521-3765
DOI:	10.1002/chem.201201232