Enantioselective Synthesis of 3,3'-Diaryl-SPINOLS by Rh-Catalyzed Asymmetric Arylation-BF3-Promoted Spirocyclization Reactions.

Enantioselective Synthesis of 3,3'-Diaryl-SPINOLS by Rh-Catalyzed Asymmetric Arylation-BF3-Promoted Spirocyclization Reactions.
Angew Chem Int Ed Engl. 2019 Jan 02;:
Authors: Yin L, Xing J, Wang Y, Shen Y, Lu T, Hayashi T, Dou X
Abstract
Enantioselective synthesis of a series of C2-symmetric 3,3'-diarylated 1,1'-spirobiindane-7,7'-diols (3,3'-Diaryl-SPINOLS) was developed via a sequential Rh-catalyzed two-fold asymmetric conjugate arylation-BF3-promoted diastereoselective spirocyclization process (>20:1 dr and >99% ee for all the examples). Some phosphoramidite ligands were prepared from the 3,3'-Ph-SPINOL and applied to several catalytic asymmetric reactions, where the 3,3'-diarylated ligands showed higher enantioselectivities than the privileged non-substituted ones.
PMID: 30600869 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - January 2, 2019 Category: Chemistry Authors: Yin L, Xing J, Wang Y, Shen Y, Lu T, Hayashi T, Dou X Tags: Angew Chem Int Ed Engl Source Type: research