Carbon Dioxide as a Protecting Group: Highly Efficient and Selective Catalytic Access to Cyclic Cis-Diol Scaffolds
The efficient and highly selective formation of a wide range of (hetero)cyclic cis-diol scaffolds using powerful aminotriphenolate- based metal catalysts is reported. The key intermediates are cyclic carbonates that are derived in high yield and with high levels of diastereo- and chemo-selectivity f...
| Autores: | , , , , , |
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| Formato: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2014 |
| País: | España |
| Recursos: | Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya) |
| Repositorio: | Recercat. Dipósit de la Recerca de Catalunya |
| OAI Identifier: | oai:recercat.cat:2072/356058 |
| Acesso em linha: | http://hdl.handle.net/2072/356058 https://doi.org/10.1002/anie.201406645 |
| Access Level: | acceso abierto |
| Palavra-chave: | 54 |
| Resumo: | The efficient and highly selective formation of a wide range of (hetero)cyclic cis-diol scaffolds using powerful aminotriphenolate- based metal catalysts is reported. The key intermediates are cyclic carbonates that are derived in high yield and with high levels of diastereo- and chemo-selectivity from the parent oxirane precursors and carbon dioxide (CO2). Deprotection of the carbonate structures affords synthetically useful cis-diol scaffolds with different ring sizes incorporating various functional groups. This atom-efficient methodology allows for simple construction of diol synthons using cheap and accessible precursors and green metal catalysts, and showcases the use of CO2 as a temporary protecting group. |
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