Título:
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Organocatalyzed Domino [3+2] Cycloaddition/Payne-Type Rearrangement using Carbon Dioxide and Epoxy Alcohols
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Autor/a:
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Sopeña, Sergio; Cozzolino, Mariachiarra; Maquilón, Cristina; Escudero-Adán, Eduardo C.; Martínez Belmonte, Marta; Kleij, Arjan W.
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Abstract:
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An unprecedented organocatalytic approach towards highly substituted cyclic carbonates from tri- and tetra-substituted oxiranes and carbon dioxide has been developed. The protocol involves the use of a simple and cheap superbase under mild, additive- and metal-free conditions towards the initial formation of a less substituted carbonate product that equilibrates to a tri- or even tetra-substituted cyclic carbonate under thermodynamic control. The latter are conveniently trapped in situ providing overall a new domino process for synthetically elusive heterocyclic scaffolds. Control experiments provide a rationale for the observed cascade reactions, which demonstrate high similarity with the well-known Payne rearrangement of epoxy alcohols. |
Fecha de creación:
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27-08-2018 |
Materia(s):
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54 |
Derechos:
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L'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons:http://creativecommons.org/licenses/by-nc-nd/4.0/ |
Páginas:
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11203 p. |
Tipo de documento:
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Artículo Artículo - Versión aceptada |
DOI:
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10.1002/anie.201803967
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