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Synlett 2014; 25(16): 2311-2315
DOI: 10.1055/s-0034-1378633
DOI: 10.1055/s-0034-1378633
cluster
Rhodium-Catalyzed Carbonylative Skeleton Rearrangement of 1,4-Enynes Tethered by a Cyclopropane Group
Further Information
Publication History
Received: 22 July 2014
Accepted after revision: 24 July 2014
Publication Date:
21 August 2014 (online)
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Abstract
The carbonylative skeleton rearrangement of 1,4 enynes tethered by a cyclopropane group proceeded smoothly in the presence of [Rh(CO)2Cl]2 under CO atmosphere to give the corresponding 1,2,4,5,6,7-hexahydrocyclopenta[a]inden-3(3bH)-one derivatives in moderate yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000083.
- Supporting Information
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References and Notes
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- 20 The crystal data of 2a have been deposited in CCDC with number 906119.
- 21 There is still another mechanism that can explain the formation of product 2a. However, this mechanism involves the formation of a very strained intermediate, which makes this mechanism seems less possible (Scheme 3).
For transition-metal-catalyzed cyclizations of 1,4-enynes, see:
For carbonylative cycloisomerisation of 1,4-enynes, see:
It has been reported that electron-deficient CO or phosphine ligands were critical to increase the π-acidity of the rhodium center, see:
Phosphine ligands have great influence on rhodium-catalyzed carbonylation and decarbonylation and a π-acidic phosphine ligand can promote decarbonylation in some cases, see: