Year: 2023
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide Since its discovery more than a century ago, the Friedel–Crafts reaction has manifested itself as a powerful method for the introduction of carbon substituents to arenes. Despite its potential generality, the scope of the reaction is intrinsically limited by the arene’s nucleophilicity, which has previously restrained the applicability of asymmetric variants to activated substrates. To overcome this fundamental limitation, we report herein an asymmetric Friedel–Crafts reaction of unactivated, purely hydrocarbon arenes, alkoxybenzenes, and heteroarenes with N, O -acetals to give enantioenriched arylglycine esters. Highly regio- and stereoselective C–C bond formation was achieved using strong and confined Brønsted acid organocatalysts, enabling the first asymmetric catalytic Friedel–Crafts reaction of simple alkylbenzenes.
DOI: 10.1021/jacs.3c05148
Institution: Max-Planck-Institut für Kohlenforschung
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $5,000
OpenAlex ID: W4384197548