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Open AccessArticle

Diastereoselective Synthesis of 7,8-Carvone Epoxides

1
Departamento de Química, Faculdade de Ciências, FibEnTech—Materiais Fibrosos e Tecnologias Ambientais, Universidade da Beira Interior, Rua Marques de Ávila e Bolama, 6201-001 Covilhã, Portugal
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Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain
3
Servicio de Difracción de Rayos X, Nucleus, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain
4
Departamento de Química Física Aplicada, Facultad de Ciencias, Universidad Autónoma de Madrid, Ciudad Universitaria de Cantoblanco, 28049 Madrid, Spain
*
Author to whom correspondence should be addressed.
Catalysts 2018, 8(6), 250; https://doi.org/10.3390/catal8060250
Received: 4 June 2018 / Revised: 15 June 2018 / Accepted: 16 June 2018 / Published: 19 June 2018
(This article belongs to the Special Issue Catalyzed Synthesis of Natural Products)
The synthesis of the two 7,8-epoxides of carvone has been attained using organocatalysis in a two-step synthetic route through a bromoester intermediate. Among the different reaction conditions tested for the bromination reaction, moderate yields and diastereoselection are achieved using proline, quinidine, and diphenylprolinol, yielding the corresponding bromoesters that were transformed separately into their epoxides, obtaining the enantiopure products. View Full-Text
Keywords: organocatalysis; aminocatalysis; proline; carvone; epoxidation; epoxide organocatalysis; aminocatalysis; proline; carvone; epoxidation; epoxide
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Pombal, S.; E. Tobal, I.; M. Roncero, A.; M. Rodilla, J.; M. Garrido, N.; Sanz, F.; Esteban, A.; Tostado, J.; F. Moro, R.; Sexmero, M.J.; G. Jambrina, P.; Diez, D. Diastereoselective Synthesis of 7,8-Carvone Epoxides. Catalysts 2018, 8, 250.

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1
Catalysts, EISSN 2073-4344, Published by MDPI AG
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