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DOI: 10.1055/s-0034-1378736
Isocyanide-Based Multicomponent Reactions: Rapid Synthesis of a 5,5-Fused Bicyclic Skeleton from α,β-Unsaturated Ketones and Allenoates
Publikationsverlauf
Received: 17. April 2015
Accepted after revision: 05. Juni 2015
Publikationsdatum:
24. Juli 2015 (online)
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Abstract
An efficient multicomponent reaction of isocyanides, allenoates, and α,β-unsaturated ketones is disclosed, thus providing rapid access for the synthesis of bicyclic skeletons. From a mechanistic standpoint, the present cycloaddition proceeds through cascade cycloaddition followed by hydration and intramolecular cyclization. Several controlled experiments are also conducted to gain further insight into the reaction mechanism; some valuable and interesting findings were observed during this process. To enrich the structural diversity, 3-(2-oxoethylene)indolinones (i.e. with an α,β-unsaturated ketone at position 3) were also found to be compatible in this reaction. In addition, this method is also characterized by its broad substrate scope, mild conditions, and high efficiency, which makes it valuable for further application.
Key words
isocyanide - multicomponent reaction - allenoate - bicyclic skeleton - α,β-unsaturated ketoneSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378736.
- Supporting Information
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For recent examples, see:
For construction of heterocycles, see: Indole:
For a review on synthesis of indoles from isocyanides, see:
Oxazole:
Imidazole:
For the synthesis of other rings, see:
For palladium-catalyzed insertion of isocyanide, see:
For other metal-catalyzed insertion, see:
For radical based examples, see:
For atom economy:
For step economy:
For redox economy:
For reviews, see:
The first step is also a formal [3+2] cycloaddition, which is similar to phosphine-catalyzed [3+2] cycloaddition with allenoate. Please see: