Stereocenter

Organic chemistry

Combinatorial chemistry

Olefin fiber

Composite number

Enantioselective synthesis

Catalysis

Carbon fibers

Medicinal chemistry

Composite material

Chemistry

Materials science

Cyclopentanes

Quaternary carbon

Brønsted–Lowry acid–base theory

Journal of the American Chemical Society

A radical-based asymmetric olefin difunctionalization strategy for rapidly forging all-carbon quaternary stereocenters α to diverse azaarenes is reported. Under cooperative photoredox and chiral Brønsted acid catalysis, cyclopropylamines with α-branched 2-vinylazaarenes can undergo a sequential two-step radical process, furnishing various valuable chiral azaarene-substituted cyclopentanes. The use of the rigid and confined C2-symmetric imidodiphosphoric acid catalysts achieves high enantio- and diastereo-selectivities for these asymmetric [3 + 2] cycloadditions.

All-Carbon Quaternary Stereocenters α to Azaarenes via Radical-Based Asymmetric Olefin Difunctionalization