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Oxyallyl cation promoted dearomative semipinacol rearrangement: a facile stereodivergent synthesis of spiro-indolines with contiguous quaternary centers.
Xie, Yu-Yang; Wang, Yun-Peng; Zhao, Xiao-Jing; Wang, Ai-Fang; Chen, Zhi-Min; Tu, Yong-Qiang.
Afiliación
  • Xie YY; School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China. tuyq@sjtu.edu.cn chenzhimin221@sjtu.edu.cn.
  • Wang YP; School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China. tuyq@sjtu.edu.cn chenzhimin221@sjtu.edu.cn.
  • Zhao XJ; School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China. tuyq@sjtu.edu.cn chenzhimin221@sjtu.edu.cn.
  • Wang AF; School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China. tuyq@sjtu.edu.cn chenzhimin221@sjtu.edu.cn.
  • Chen ZM; School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China. tuyq@sjtu.edu.cn chenzhimin221@sjtu.edu.cn.
  • Tu YQ; School of Chemistry and Chemical Engineering, Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240, P. R. China. tuyq@sjtu.edu.cn chenzhimin221@sjtu.edu.cn and State Key Laboratory of
Chem Commun (Camb) ; 57(54): 6632-6635, 2021 Jul 06.
Article en En | MEDLINE | ID: mdl-34124740
ABSTRACT
A novel oxyallyl cation promoted semipinacol rearrangement of indole-type allylic alcohols was disclosed for the stereodivergent synthesis of spiro-indolines. A variety of spiro-indolines were obtained with moderate to good yields. Three contiguous stereocenters, two of which are vicinal quaternary centers, were effectively formed with good diastereoselectivity. It is worth noting that two diastereoisomers of rearranged products can be readily achieved by easily regulating the reaction conditions. This method may provide an applicable approach for the synthesis of natural indole alkaloids.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Commun (Camb) Asunto de la revista: QUIMICA Año: 2021 Tipo del documento: Article
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Commun (Camb) Asunto de la revista: QUIMICA Año: 2021 Tipo del documento: Article