Diastereoselective Synthesis of 7,8-Carvone Epoxides

Catalysts

Pablo G. Jambrina¹  Ignacio E. Tobal²  David Diez²  MariaJose Sexmero²  Alejandro M. Roncero²  Narciso M. Garrido²  Alberto Esteban²  Jaime Tostado²  Rosalina F. Moro²  Sofia Pombal³  Jesus M. Rodilla³  Francisca Sanz⁴ 

[1] Departamento de Química Física Aplicada, Facultad de Ciencias, Universidad Autónoma de Madrid, Ciudad Universitaria de Cantoblanco, 28049 Madrid, Spain;Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain;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;Servicio de Difracción de Rayos X, Nucleus, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain;

关键词: organocatalysis;    aminocatalysis;    proline;    carvone;    epoxidation;    epoxide;   

DOI  :  10.3390/catal8060250

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown