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Ir/Zn-cocatalyzed chemo- and atroposelective [2+2+2] cycloaddition for construction of C─N axially chiral indoles and pyrroles.
Yang, Jian; Xie, Zhong-Yang; Ye, Yu-Jie; Ye, Sheng-Bing; Wang, Yi-Bo; Wang, Wen-Tao; Qian, Peng-Cheng; Song, Ren-Jie; Sun, Qing; Ye, Long-Wu; Li, Long.
Afiliación
  • Yang J; College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.
  • Xie ZY; College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.
  • Ye YJ; College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.
  • Ye SB; College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.
  • Wang YB; College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.
  • Wang WT; College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.
  • Qian PC; College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.
  • Song RJ; Wenzhou Key Laboratory of Technology and Application of Environmental Functional Materials, Institute of New Materials and Industry Technology, Wenzhou University, Wenzhou 325000, China.
  • Sun Q; Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China.
  • Ye LW; Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China.
  • Li L; State Key Laboratory of Physical Chemistry of Solid Surfaces and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
Sci Adv ; 9(51): eadk1704, 2023 Dec 22.
Article en En | MEDLINE | ID: mdl-38117883
ABSTRACT
Here, an Ir/Zn-cocatalyzed atroposelective [2+2+2] cycloaddition of 1,6-diynes and ynamines was developed, forging various functionalized C─N axially chiral indoles and pyrroles in generally good to excellent yields (up to 99%), excellent chemoselectivities, and high enantioselectivities (up to 98% enantiomeric excess) with wide substrate scope. This cocatalyzed strategy not only provided an alternative promising and reliable way for asymmetric alkyne [2+2+2] cyclotrimerization in an easy handle but also settled the issues of previous [Rh(COD)2]BF4-catalyzed system on the construction of C─N axial chirality such as complex operations, limited substrate scope, and low efficiency. In addition, control experiments and theoretical calculations disclosed that Zn(OTf)2 markedly reduced the barrier of migration insertion to significantly increase reaction efficiency, which was distinctly different from previous work on the Lewis acid for improving reaction yield through accelerating oxidative addition and reductive elimination.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Sci Adv Año: 2023 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos
Texto completo
Añadir a Mi BVS
Imprimir
XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Sci Adv Año: 2023 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos