Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 43, Pages 13495-13498Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201607305
Keywords
asymmetric catalysis; C-H activation; photochemistry; radicals; rhodium
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Funding
- Deutsche Forschungsgemeinschaft [ME 1805/13-1]
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This work demonstrates how photoredox-mediated C(sp(3))-H activation through radical translocation can be combined with asymmetric catalysis. Upon irradiation with visible light, ,-unsaturated N-acylpyrazoles react with N-alkoxyphthalimides in the presence of a rhodium-based chiral Lewis acid catalyst and the photosensitizer fac-[Ir(ppy)(3)] to provide a C-C bond-formation product with high enantioselectivity (up to 97% ee) and, where applicable, with some diastereoselectivity (3.0:1 d.r.). Mechanistically, the synthetic strategy exploits a radical translocation (1,5-hydrogen transfer) from an oxygen-centered to a carbon-centered radical with a subsequent stereocontrolled radical alkene addition.
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