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Catalytic Enantioselective Steglich-Type Rearrangement of Enol Lactones: Asymmetric Synthesis of Spirocyclic 1,3-Diketones.
Zhang, Xiao-Yan; Lu, Ka; Guo, Bao-Kuan; Shao, Ya-Ping; Wang, Hong; Zhang, Fu-Min; Tu, Yong-Qiang; Zhang, Xiao-Ming.
Afiliación
  • Zhang XY; State Key Laboratory of Applied Organic Chemistry, School of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
  • Lu K; State Key Laboratory of Applied Organic Chemistry, School of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
  • Guo BK; State Key Laboratory of Applied Organic Chemistry, School of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
  • Shao YP; State Key Laboratory of Applied Organic Chemistry, School of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
  • Wang H; School of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
  • Zhang FM; State Key Laboratory of Applied Organic Chemistry, School of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
  • Tu YQ; State Key Laboratory of Applied Organic Chemistry, School of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
  • Zhang XM; Beijing National Laboratory for Molecular Sciences, Beijing 100109, P. R. China.
J Org Chem ; 87(22): 15031-15041, 2022 11 18.
Article en En | MEDLINE | ID: mdl-36325975
An example of asymmetric Steglich-type rearrangement of enol lactones is reported. This highly enantioselective acyl transfer reaction is catalyzed by chiral isothiourea at ambient temperature and provides a useful synthetic approach to access enantioenriched spirotricyclic ß,ß'-diketones from a broad range of indanone or tetralone-derived lactones. Preliminary mechanistic studies suggest the initial formation of an N-acylated iminium cation intermediate that induces a following facial selective condensation.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Cetonas / Lactonas Idioma: En Revista: J Org Chem Año: 2022 Tipo del documento: Article Pais de publicación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Cetonas / Lactonas Idioma: En Revista: J Org Chem Año: 2022 Tipo del documento: Article Pais de publicación: Estados Unidos