The DOI matches its Crossref record; 25 of the 25 references it cites were found in a registry or an index.
Gold-Catalyzed [4C+2C] Cycloadditions of Allenedienes, including an Enantioselective Version with New Phosphoramidite-Based Catalysts: Mechanistic Aspects of the Divergence between [4C+3C] and [4C+2C] Pathways
Abstract
Gold(I) complexes featuring electron acceptor ligands such as phosphites and phosphoramidites catalyze the [4C+2C] intramolecular cycloaddition of allenedienes. The reaction is chemo- and stereoselective, and provides trans-fused bicyclic cycloadducts in good yields. Moreover, using novel chiral phosphoramidite-based gold catalysts it is possible to perform the reaction with excellent enantioselectivity. Experimental and theoretical data dismiss a cationic mechanism involving intermediate II and suggest that the formation of the [4C+2C] cycloadducts might arise from a 1,2-alkyl migration (ring contraction) in a cycloheptenyl Au-carbene intermediate (IV), itself arising from a [4C+3C] concerted cycloaddition of the allenediene. Therefore, these [4C+2C] allenediene cycloadditions and the previously reported [4C+3C] counterparts most likely share such cycloaddition step, differing in the final 1,2-migration step.
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Metadata
- Authors
- Alonso, I., Trillo, B., López, F., Montserrat, S., Ujaque, G., Castedo, L., Lledós, A., & Mascareñas, J. L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-08-21
- Volume
- 131
- Issue
- 36
- Pages
- 13020-13030
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2011091258
- Cited by
- 277
- References
- 25
- FWCI
- 15.64
- Type
- journal article
- Language
- en
- Open access
- closed
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