Chiral Indoline‐2‐carboxylic Acid Enables Highly Enantioselective Catellani‐type Annulation with 4‐(Bromomethyl)cyclohexanone
Xinmeng Chen, Ling Zhu, Dian‐Feng Chen, Liu‐Zhu Gong
Abstract
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.
Topics & Concepts
CyclohexanoneEnantioselective synthesisAnnulationChemistryCarboxylic acidArylIndolineStereochemistryOrganic chemistryCatalysisAlkylAlkaloids: synthesis and pharmacologyAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization Methods