Organocatalyzed Domino [3+2] Cycloaddition/Payne‐Type Rearrangement using Carbon Dioxide and Epoxy Alcohols |
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Authors: | Sergio Sopeña Mariachiara Cozzolino Cristina Maquilón Dr. Eduardo C. Escudero‐Adán Dr. Marta Martínez Belmonte Prof. Dr. Arjan W. Kleij |
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Affiliation: | 1. Institute of Chemical Research of Catalonia (ICIQ), the Barcelona Institute of Science and Technology, Tarragona, Spain;2. Catalan Institute of Research and Advanced Studies (ICREA), Barcelona, Spain |
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Abstract: | An unprecedented organocatalytic approach towards highly substituted cyclic carbonates from tri‐ and tetrasubstituted 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 tetrasubstituted 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 similarity to the well‐known Payne rearrangement of epoxy alcohols. |
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Keywords: | carbon dioxide epoxides heterocycles organocatalysis rearrangements |
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