Copper(II)- and Palladium(II)-Catalyzed Enantioselective Claisen Rearrangement of Allyloxy- and Propargyloxy-Indoles to Quaternary Oxindoles and Spirocyclic Lactones
| Autor: | Elizabeth C. Linton, Joshua Deitch, Simon Berritt, Marisa C. Kozlowski, Trung Cao |
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| Rok vydání: | 2012 |
| Předmět: |
Indoles
Organic Chemistry Enantioselective synthesis chemistry.chemical_element Stereoisomerism Copper Article Catalysis Oxindoles Substrate Specificity Claisen rearrangement Lactones chemistry.chemical_compound chemistry Organic chemistry Spiro Compounds Lewis acids and bases Palladium Lewis Acids BINAP |
| Zdroj: | Scopus-Elsevier |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo302039n |
| Popis: | In this Article, a strategy to obtain highly enantioselective catalysts for the Claisen rearrangement of allyloxy- and propargyloxy-indoles is outlined. Ultimately, copper BOX and palladium BINAP or PHOX catalysts were discovered as superior in catalyzing Claisen rearrangements of allyloxy- or proparyloxy-substituted indoles to generate oxindoles bearing allyl- or allenyl-substituted quaternary centers. This method proved to be tolerant of a broad range of functional groups. Tandem reactions of the silyl-allene products provide rapid access to a variety of spirocyclic oxindoles in one operation. |
| Databáze: | OpenAIRE |
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