Violet-light excitation of an in-situ formed chiral iminium ion transforms this well-established electrophilic intermediate <b>I </b>into a powerful oxidant <b>I*</b>. The chiral amine catalyst activates both the substrate, facilitating light absorption, and controls the stereochemistry of the ensuing bond-forming events. Thus, through a single-electron transfer (SET) manifold α,β-unsaturated aldehydes can react with unconventional partners in an enantioselective manner. Presented in this work are cascade reactions, triggered by the SET chemistry of photo-excited iminium ion, affording enantioenriched aldehyde products bearing functionalized carbo- and heterocycles.

Excited-state reactivity of chiral iminium ions to perform enantioselective cascade reactions

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.