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Chiral spirosiladiphosphines: ligand development and applications in Rh-catalyzed asymmetric hydrosilylation/cyclization of 1,6-enynes with enhanced reactivity.
Hou, Fei; Liu, Minjie; Ru, Tong; Tan, Zequn; Ning, Yingtang; Chen, Fen-Er.
Afiliación
  • Hou F; Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University 200433 Shanghai China ningyt@fudan.edu.cn rfchen@fudan.edu.cn.
  • Liu M; Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs 200433 Shanghai China.
  • Ru T; Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University 200433 Shanghai China ningyt@fudan.edu.cn rfchen@fudan.edu.cn.
  • Tan Z; Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs 200433 Shanghai China.
  • Ning Y; Engineering Center of Catalysis and Synthesis for Chiral Molecules, Fudan University 200433 Shanghai China ningyt@fudan.edu.cn rfchen@fudan.edu.cn.
  • Chen FE; Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs 200433 Shanghai China.
Chem Sci ; 14(17): 4641-4646, 2023 May 03.
Article en En | MEDLINE | ID: mdl-37152270
Spirodiphosphines have been successfully applied in various asymmetric catalytic transformations. However, controlling the coordinating conformations by the direct displacement of the spiro atom remains elusive. Herein, we report the application of Si-centered spirodiphosphine (Si-SDP) ligands in the enantioselective hydrosilylation/cyclization of 1,6-enynes. The Si-SDPs showed superior reactivity to existing C2-symmetric diphosphines, allowing the generation of a range of chiral pyrrolidines with high yields and enantioselectivity (up to 96% yield and 92% ee) at room temperature with low catalyst loading. The mechanistic observations were consistent with the modified Chalk-Harrod mechanism, and the high reactivity of Si-SDPs was further leveraged for the room-temperature Rh-catalyzed hydrosilylation of alkynes.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2023 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
Añadir a Mi BVS
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2023 Tipo del documento: Article Pais de publicación: Reino Unido