Enantioselective Synthesis of 3,3′-Diaryl-SPINOLs: Rhodium-Catalyzed Asymmetric Arylation/BF3-Promoted Spirocyclization Sequence
Long Yin
Department of Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 211198 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Junhao Xing
Department of Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 211198 China
These authors contributed equally to this work.
Search for more papers by this authorYuhan Wang
Department of Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 211198 China
Search for more papers by this authorYue Shen
Department of Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 211198 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Tao Lu
Department of Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 211198 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Tamio Hayashi
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorCorresponding Author
Prof. Dr. Xiaowei Dou
Department of Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 211198 China
Search for more papers by this authorLong Yin
Department of Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 211198 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Junhao Xing
Department of Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 211198 China
These authors contributed equally to this work.
Search for more papers by this authorYuhan Wang
Department of Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 211198 China
Search for more papers by this authorYue Shen
Department of Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 211198 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Tao Lu
Department of Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 211198 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Tamio Hayashi
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore, 637371 Singapore
Search for more papers by this authorCorresponding Author
Prof. Dr. Xiaowei Dou
Department of Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 211198 China
Search for more papers by this authorGraphical Abstract
Going for a ′SPIN′: The enantioselective synthesis of a series of 3,3′-diarylated 1,1′-spirobiindane-7,7′-diols (3,3′-diaryl-SPINOLs) was developed using a sequential Rh-catalyzed twofold asymmetric conjugate arylation/BF3-promoted diastereoselective spirocyclization. Some phosphoramidite ligands were prepared from the 3,3′-Ph-SPINOL and applied to several catalytic asymmetric reactions, and the 3,3′-diarylated ligands showed higher enantioselectivities than the privileged nonsubstituted ligands.
Abstract
The enantioselective synthesis of a series of C2-symmetric 3,3′-diarylated 1,1′-spirobiindane-7,7′-diols (3,3′-diaryl-SPINOLs) was developed by sequential Rh-catalyzed twofold asymmetric conjugate arylation/BF3-promoted diastereoselective spirocyclization (>20:1 d.r. and >99 % ee for all examples). Some phosphoramidite ligands were prepared from the 3,3′-Ph-SPINOL and applied to several catalytic asymmetric reactions, and the 3,3′-diarylated ligands showed higher enantioselectivities than the privileged nonsubstituted ligands.
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