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Enantioselective Synthesis of 3,3'-Diaryl-SPINOLs: Rhodium-Catalyzed Asymmetric Arylation/BF3 -Promoted
Long Yin1, Junhao Xing1, Yuhan Wang1
1Department of Chemistry and State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing, 211198, China.
Angewandte Chemie (International Ed. in English)
|January 3, 2019
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.