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Palladium‐Catalyzed Enantioselective C−H Olefination to Access Planar‐Chiral Cyclophanes by Dynamic Kinetic Resolution.
- Source :
-
Angewandte Chemie International Edition . 12/18/2023, Vol. 62 Issue 51, p1-7. 7p. - Publication Year :
- 2023
-
Abstract
- Planar‐chiral cyclophanes have received increasing attention for drug discovery and catalyst design. However, the catalytically asymmetric synthesis of planar‐chiral cyclophanes has been a longstanding challenge. We describe the first Pd(II)‐catalyzed enantioselective C−H olefination of prochiral cyclophanes. The low rotational barrier of less hindered benzene ring in the substrates allows the reaction to proceed through a dynamic kinetic resolution. This approach exhibits broad substrate scope, providing the planar‐chiral cyclophanes in high yields (up to 99 %) with excellent enantioselectivities (up to >99 % ee). The ansa chain length scope studies reveal that the chirality of the cyclophanes arises from the bond rotation constraint of the benzene ring around the macrocycle plane, rather than the C−N axis. The C−H activation approach is also applicable to the late‐stage modification of bioactive molecules and pharmaceuticals. [ABSTRACT FROM AUTHOR]
- Subjects :
- *CYCLOPHANES
*DRUG discovery
*KINETIC resolution
*ASYMMETRIC synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 62
- Issue :
- 51
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 174157670
- Full Text :
- https://doi.org/10.1002/anie.202315603