Journal
SCIENCE CHINA-CHEMISTRY
Volume 62, Issue 11, Pages 1512-1518Publisher
SCIENCE PRESS
DOI: 10.1007/s11426-019-9584-x
Keywords
photoredox catalysis; asymmetric catalysis; visible light; enantioconvergent; radical recombination; chiral-at-metal; rhodium
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Racemic alpha-chloro imidazol-2-yl-ketones undergo an enantioconvergent photoactivated C-C bond formation with N-aryl glycines catalyzed by a single bis-cyclometalated chiral-at-rhodium catalyst in yields of up to 80% and up to 98% enantiomeric excess (ee). Control experiments support a mechanism which is initiated by a single electron transfer from N-aryl glycinate to the photochemically excited rhodium-bound alpha-chloro imidazol-2-yl-ketone, followed by chloride fragmentation of the alpha-chloroketone, decarboxylation of the glycinate, and a subsequent highly stereocontrolled radical-radical coupling. This work showcases the ability of the chiral rhodium catalyst to serve a dual function as chiral Lewis acid and at the same time as the photoredox active species upon substrate binding.
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