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Organocatalytic Enantioselective Conia-Ene-Type Carbocyclization of Ynamide Cyclohexanones: Regiodivergent Synthesis of Morphans and Normorphans.
Xu, Yin; Sun, Qing; Tan, Tong-De; Yang, Ming-Yang; Yuan, Peng; Wu, Shao-Qi; Lu, Xin; Hong, Xin; Ye, Long-Wu.
Afiliación
  • Xu Y; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory for Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
  • Sun Q; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory for Theoretical and Computational Chemistry of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
  • Tan TD; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory for Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
  • Yang MY; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory for Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
  • Yuan P; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory for Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
  • Wu SQ; Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
  • Lu X; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory for Theoretical and Computational Chemistry of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
  • Hong X; Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
  • Ye LW; State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory for Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
Angew Chem Int Ed Engl ; 58(45): 16252-16259, 2019 11 04.
Article en En | MEDLINE | ID: mdl-31444882
Described herein is an organocatalytic enantioselective desymmetrizing cycloisomerization of arylsulfonyl-protected ynamide cyclohexanones, representing the first metal-free asymmetric Conia-ene-type carbocyclization. This method allows the highly efficient and atom-economical construction of a range of valuable morphans with wide substrate scope and excellent enantioselectivity (up to 97 % ee). In addition, such a cycloisomerization of alkylsulfonyl-protected ynamide cyclohexanones can lead to the divergent synthesis of normorphans as the main products with high enantioselectivity (up to 90 % ee). Moreover, theoretical calculations are employed to elucidate the origins of regioselectivity and enantioselectivity.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2019 Tipo del documento: Article País de afiliación: China Pais de publicación: Alemania
Texto completo
Añadir a Mi BVS
Imprimir
XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2019 Tipo del documento: Article País de afiliación: China Pais de publicación: Alemania