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 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.

Automated summary

The chiral indoline-2-carboxylic acid enables a highly enantioselective Catellani-type annulation, directly assembling a diverse range of chiral all-carbon bridged ring systems with high levels of stereochemical control through coordinating orientation to the arylpalladium(II) center identified by control experiments and DFT calculations.