Chiral Indoline‐2‐carboxylic Acid Enables Highly Enantioselective Catellani‐type Annulation with 4‐(Bromomethyl)cyclohexanone

Chiral indoline‐2‐carboxylic acid has been identified to enable a highly enantioselective Catellani‐type annulation of (hetero)aryl, alkenyl triflate and conjugated vinyl iodides with 4‐(bromomethyl)cyclohexanone, directly assembling a diverse range of chiral all‐carbon bridged ring systems. Control...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2021-11, Vol.60 (47), p.24844-24848
Main Authors: Chen, Xin‐Meng, Zhu, Ling, Chen, Dian‐Feng, Gong, Liu‐Zhu
Format: Article
Language:English
Subjects:
Amino acids
asymmetric Catellani annulation
Carboxylic acids
Chemical reactions
chiral amines
cooperative catalysis
Cyclohexanone
C−H activation
Enantiomers
Iodides
Organic chemistry
palladium
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Summary:Chiral indoline‐2‐carboxylic acid has been identified to enable a highly enantioselective Catellani‐type annulation of (hetero)aryl, alkenyl triflate and conjugated vinyl iodides with 4‐(bromomethyl)cyclohexanone, directly assembling a diverse range of chiral all‐carbon bridged ring systems. Control experiments and DFT calculations suggest that the coordinating orientation of the chiral amino acid to the arylpalladium(II) center allows for high levels of stereochemical control. Chiral indoline‐2‐carboxylic acid enables a highly enantioselective Catellani‐type annulation of (hetero)aryl iodides, alkenyl triflate and conjugated vinyl iodides with 4‐(bromomethyl)cyclohexanone, directly assembling a diverse range of chiral all‐carbon bridged ring systems.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202109771