Stereoselective synthesis of functionalized bicyclic scaffolds by passerini 3-center-2-component reactions of cyclic ketoacids
| Autor: | Cioc, Razvan C., Estevez, Veronica, van der Niet, Daan J., Vande Velde, Christophe M. L., Turrini, Nikolaus G., Hall, Melanie, Faber, Kurt, Ruijter, Eelco, Orru, Romano V. A. |
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| Přispěvatelé: | Organic Chemistry, AIMMS |
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: | |
| Zdroj: | European journal of organic chemistry Cioc, R C, Estevez, V, van der Niet, D J, Vande Velde, C M L, Turrini, N G, Hall, M, Faber, K, Ruijter, E & Orru, R V A 2017, ' Stereoselective Synthesis of Functionalized Bicyclic Scaffolds by Passerini 3-Center-2-Component Reactions of Cyclic Ketoacids ', European Journal of Organic Chemistry, vol. 2017, no. 9, pp. 1262-1271 . https://doi.org/10.1002/ejoc.201601432 European Journal of Organic Chemistry, 2017(9), 1262-1271. Wiley-VCH Verlag |
| ISSN: | 1434-193X |
| DOI: | 10.1002/ejoc.201601432 |
| Popis: | We report the use of bifunctional starting materials (ketoacids) in a diastereoselective Passerini three-center-two-component reaction. Study of the reaction scope revealed the required structural features for stereoselectivity in the isocyanide addition. In this system, an interesting isomerization of the primary Passerini product - the alpha-carboxamido lactone - into an atypical product, an alpha-hydroxy imide, was found to occur under acidic conditions. Furthermore, enantioenriched Passerini products can be generated from an enantioenriched ketoacid obtained by chemoenzymatic synthesis. |
| Databáze: | OpenAIRE |
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