Journal
PURE AND APPLIED CHEMISTRY
Volume 86, Issue 3, Pages 265-272Publisher
WALTER DE GRUYTER GMBH
DOI: 10.1515/pac-2014-5029
Keywords
asymmetric catalysis; C-H functionalization; cooperative effects; heterocycles; OMCOS-17; palladium
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Transition-metal-catalyzed C-H functionalizations have emerged as complementary and powerful tools to access molecular complexity from widely available starting materials. Herein, we present a strategy for asymmetric intramolecular Pd(0)-catalyzed C-H functionalizations. The outlined reactivity is based on the cooperative effect between a chiral phosphorous ligand and a carboxylate base acting as a relay of chirality during the enantio-discriminating concerted metalation deprotonation step. This approach allows the enantioselective construction of a range of important semi-saturated chiral nitrogen-containing heterocycles such as indolines, tetrahydroquinolines, and dibenzazepinones.
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