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Copper-Catalyzed Enantioselective 1,2-Allylation of Azadienes with Allylboronates.
Dong, Zhi-Hong; Li, Shu; Long, Teng; Zhan, Jie; Ruan, Cheng-Kai; Yan, Xu; Chu, Wen-Dao; Yuan, Kun; Liu, Quan-Zhong.
Afiliación
  • Dong ZH; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, P.R. China.
  • Li S; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, P.R. China.
  • Long T; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, P.R. China.
  • Zhan J; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, P.R. China.
  • Ruan CK; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, P.R. China.
  • Yan X; College of Chemical Engineering and Technology, Key Laboratory for New Molecule Materials Design and Function of Gansu Universities, Tianshui Normal University, Tianshui, Gansu 741001, P.R. China.
  • Chu WD; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, P.R. China.
  • Yuan K; College of Chemical Engineering and Technology, Key Laboratory for New Molecule Materials Design and Function of Gansu Universities, Tianshui Normal University, Tianshui, Gansu 741001, P.R. China.
  • Liu QZ; Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, P.R. China.
Org Lett ; 26(15): 3235-3240, 2024 Apr 19.
Article en En | MEDLINE | ID: mdl-38557113
ABSTRACT
Catalytic asymmetric 1,2-allylation of aurone-derived azadienes is very difficult to achieve due to the driving force for aromatization and the greater steric hindrance of 1,2-addition compared with 1,4-addition. By taking advantage of the ability of nitrogen ligated metal complexes, we successfully demonstrated the first example of copper-catalyzed 1,2-allylation of azadienes with allylboronates for the highly enantioselective synthesis of homoallylic amines. Meanwhile, the enantioenriched 1,4-addition products could also be obtained through a subsequent 3,3-sigmatropic rearrangement of the 1,2-addition products. Extensive DFT calculations were carried out to elucidate the origins of high regioselectivity (1,2- vs 1,4-) and enantioselectivity.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2024 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 Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2024 Tipo del documento: Article Pais de publicación: Estados Unidos