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Enantioselective Synthesis of 3,3′‐Diaryl‐SPINOLs: Rhodium‐Catalyzed Asymmetric Arylation/BF 3 ‐Promoted Spirocyclization Sequence
Author(s) -
Yin Long,
Xing Junhao,
Wang Yuhan,
Shen Yue,
Lu Tao,
Hayashi Tamio,
Dou Xiaowei
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201812266
Subject(s) - enantioselective synthesis , phosphoramidite , catalysis , rhodium , chemistry , conjugate , combinatorial chemistry , stereochemistry , sequence (biology) , organic chemistry , mathematics , dna , mathematical analysis , biochemistry , oligonucleotide
The enantioselective synthesis of a series of C 2 ‐symmetric 3,3′‐diarylated 1,1′‐spirobiindane‐7,7′‐diols (3,3′‐diaryl‐SPINOLs) was developed by sequential Rh‐catalyzed twofold asymmetric conjugate arylation/BF 3 ‐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.