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Bifunctional Phosphonium Salt Directed Enantioselective Formal [4 + 1] Annulation of Hydroxyl-Substituted para-Quinone Methides with α-Halogenated Ketones.
Tan, Jian-Ping; Yu, Peiyuan; Wu, Jia-Hong; Chen, Yuan; Pan, Jianke; Jiang, Chunhui; Ren, Xiaoyu; Zhang, Hong-Su; Wang, Tianli.
Afiliación
  • Tan JP; Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , P. R. China.
  • Yu P; Department of Chemistry and Shenzhen Grubbs Institute , Southern University of Science and Technology , Shenzhen , China.
  • Wu JH; Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , P. R. China.
  • Chen Y; Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , P. R. China.
  • Pan J; Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , P. R. China.
  • Jiang C; Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , P. R. China.
  • Ren X; School of Environmental and Chemical Engineering , Jiangsu University of Science and Technology , 2 Mengxi Road , Zhenjiang 212003 , P. R. China.
  • Zhang HS; Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , P. R. China.
  • Wang T; Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , P. R. China.
Org Lett ; 21(18): 7298-7302, 2019 Sep 20.
Article en En | MEDLINE | ID: mdl-31490078
A highly diastereo- and enantioselective [4 + 1] cycloaddition of para-quinone methides to α-halogenated ketones was realized by bifunctional phosphonium salt catalysis, furnishing functionalized 2,3-dihydrobenzofurans in high yields and excellent stereoselectivities (>20:1 dr and up to >99.9% ee). Mechanistic observations suggested that the reaction underwent a cascade intermolecular substitution/intramolecular 1,6-addition process. DFT calculations revealed the presence of multiple H-bonding interactions between the catalyst and the enolate intermediate in the stereodetermining transition states.

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2019 Tipo del documento: Article Pais de publicación: Estados Unidos

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2019 Tipo del documento: Article Pais de publicación: Estados Unidos