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Catalytic asymmetric Michael/cyclization reaction of 3-isothiocyanato thiobutyrolactone: an approach to the construction of a library of bispiro[pyrazolone-thiobutyrolactone] skeletons.
Liu, Ren-Ming; Zhang, Min; Han, Xiao-Xue; Liu, Xiong-Li; Pan, Bo-Wen; Tian, You-Ping; Peng, Li-Jun; Yuan, Wei-Cheng.
Afiliación
  • Liu RM; National & Local Joint Engineering Research Center for the Exploitation of Homology Resources of Southwest Medicine and Food, Guizhou University, Guiyang, Guizhou 550025, P. R. China. xlliu1@gzu.edu.cn.
  • Zhang M; National & Local Joint Engineering Research Center for the Exploitation of Homology Resources of Southwest Medicine and Food, Guizhou University, Guiyang, Guizhou 550025, P. R. China. xlliu1@gzu.edu.cn.
  • Han XX; National & Local Joint Engineering Research Center for the Exploitation of Homology Resources of Southwest Medicine and Food, Guizhou University, Guiyang, Guizhou 550025, P. R. China. xlliu1@gzu.edu.cn.
  • Liu XL; National & Local Joint Engineering Research Center for the Exploitation of Homology Resources of Southwest Medicine and Food, Guizhou University, Guiyang, Guizhou 550025, P. R. China. xlliu1@gzu.edu.cn.
  • Pan BW; College of Pharmaceutical Sciences, Guizhou University of Traditional Chinese Medicine, Guiyang, 550025, China.
  • Tian YP; College of Pharmaceutical Sciences, Guizhou University of Traditional Chinese Medicine, Guiyang, 550025, China.
  • Peng LJ; National & Local Joint Engineering Research Center for the Exploitation of Homology Resources of Southwest Medicine and Food, Guizhou University, Guiyang, Guizhou 550025, P. R. China. xlliu1@gzu.edu.cn.
  • Yuan WC; Innovation Research Center of Chiral Drugs, Institute for Advanced Study, School of Pharmacy, Chengdu University, Chengdu 610106, China.
Org Biomol Chem ; 20(25): 5060-5065, 2022 06 29.
Article en En | MEDLINE | ID: mdl-35703322
Here, we demonstrate the first example of 3-isothiocyanato thiobutyrolactone serving as a useful building block in the Michael/cyclization reaction with alkylidene pyrazolones for the enantioselective construction of optically active structural bispiro[pyrazolone-thiobutyrolactone] skeletons containing three contiguous stereocenters with two spiroquaternary stereocenters. These products were smoothly afforded in up to 90% yield, >20 : 1 dr and >99% ee with chiral squaramide as the catalyst under mild conditions. Notably, this is also the first example of the merger of a spirocyclic pyrazolone scaffold with a spirocyclic thiobutyrolactone scaffold, potentially useful in medicinal chemistry.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Pirazolonas Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2022 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Pirazolonas Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2022 Tipo del documento: Article Pais de publicación: Reino Unido