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Conversion of two stereocenters to one or two chiral axes: atroposelective synthesis of 2,3-diarylbenzoindoles.
Hu, Yu-Long; Wang, Zhe; Yang, Hui; Chen, Jie; Wu, Zi-Bo; Lei, Yibo; Zhou, Ling.
Afiliación
  • Hu YL; Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education , Department of Chemistry & Materials Science , National Demonstration Center for Experimental Chemistry Education , Northwest University , Xi'an 710127 , P. R. China . Email: zhoul@nwu.edu.cn.
  • Wang Z; Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education , Department of Chemistry & Materials Science , National Demonstration Center for Experimental Chemistry Education , Northwest University , Xi'an 710127 , P. R. China . Email: zhoul@nwu.edu.cn.
  • Yang H; Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education , Department of Chemistry & Materials Science , National Demonstration Center for Experimental Chemistry Education , Northwest University , Xi'an 710127 , P. R. China . Email: zhoul@nwu.edu.cn.
  • Chen J; Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education , Department of Chemistry & Materials Science , National Demonstration Center for Experimental Chemistry Education , Northwest University , Xi'an 710127 , P. R. China . Email: zhoul@nwu.edu.cn.
  • Wu ZB; Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education , Department of Chemistry & Materials Science , National Demonstration Center for Experimental Chemistry Education , Northwest University , Xi'an 710127 , P. R. China . Email: zhoul@nwu.edu.cn.
  • Lei Y; Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education , Department of Chemistry & Materials Science , National Demonstration Center for Experimental Chemistry Education , Northwest University , Xi'an 710127 , P. R. China . Email: zhoul@nwu.edu.cn.
  • Zhou L; Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education , Department of Chemistry & Materials Science , National Demonstration Center for Experimental Chemistry Education , Northwest University , Xi'an 710127 , P. R. China . Email: zhoul@nwu.edu.cn.
Chem Sci ; 10(28): 6777-6784, 2019 Jul 28.
Article en En | MEDLINE | ID: mdl-31391898
Central-to-axial chirality conversion provides efficient access to axially chiral compounds, and several examples regarding the conversion of one, two or four stereocenters to one axis have been reported. Herein, we report the conversion of two stereocenters to one or two chiral axes for the first time. In this study, a new class of enantiomerically enriched 2,3-diarylbenzoindoles was efficiently synthesized using a chiral phosphoric acid-catalyzed [3 + 2] formal cycloaddition and a mild DDQ oxidation strategy. Moreover, a speculative model of the central-to-axial chirality conversion outcome was proposed based on preliminary mechanistic studies and DFT calculations. Potentially, using this strategy, useful chiral phosphine ligand can be synthesized smoothly (99% ee).
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2019 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2019 Tipo del documento: Article Pais de publicación: Reino Unido