Cage‐Shaped Phosphites Having C3‐Symmetric Chiral Environment: Steric Control of Lewis Basicity and Application as Chiral Ligands in Rhodium‐Catalyzed Conjugate Additions

Designing chiral ligands with an axial symmetry higher than C2‐rotational symmetry is one of the most crucial approaches to improving enantioselectivity in asymmetric synthesis. Herein, C3‐symmetric chiral cage‐shaped phosphites are reported. Their Lewis basicity and chiral environment are precisely...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2023-12, Vol.29 (67), p.e202302611-n/a
Main Authors: Liu, Xiao, Tomita, Kazuma, Konishi, Akihito, Yasuda, Makoto
Format: Article
Language:English
Subjects:
1,4-addition
Asymmetric synthesis
Asymmetry
Basicity
C3-symmetric ligand
cage-shaped phosphite
Cages
Chemical synthesis
Chemistry
chiral Lewis base
Conjugates
Enantiomers
Inorganic salts
Ligands
Rhodium
rhodium catalyst
Symmetry
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Designing chiral ligands with an axial symmetry higher than C2‐rotational symmetry is one of the most crucial approaches to improving enantioselectivity in asymmetric synthesis. Herein, C3‐symmetric chiral cage‐shaped phosphites are reported. Their Lewis basicity and chiral environment are precisely controlled by the tethered group. The cage‐shaped phosphites successfully worked as chiral ligands in Rh‐catalyzed asymmetric conjugate additions, realizing acceptable yields with excellent enantioselectivity, and were used to synthesize a pharmacologically important molecule. C3‐symmetric chiral cage‐shaped phosphites were developed as a new type of chiral ligand. Their Lewis basicity and chiral environment are precisely controlled by the tethered group. The cage‐shaped phosphites successfully worked as chiral ligands in Rh‐catalyzed asymmetric conjugate additions, realizing acceptable yields with excellent enantioselectivity, and were used to synthesize a pharmacologically important molecule.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202302611