Journal
SCIENCE
Volume 352, Issue 6284, Pages 433-437Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aaf1983
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Funding
- Netherlands Organization for Scientific Research NWO-Vidi grant
- Netherlands Organization for Scientific Research NWO-ECHO grant
- Ministry of Education, Culture and Science Gravity program [024.001.035]
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Catalytic asymmetric conjugate addition reactions represent a powerful strategy to access chiral molecules in contemporary organic synthesis. However, their applicability to conjugated alkenyl-N-heteroaromatic compounds, of particular interest in medicinal chemistry, has lagged behind applications to other substrates. We report a highly enantioselective and chemoselective catalytic transformation of a wide range of beta-substituted conjugated alkenyl-N-heteroaromatics to their corresponding chiral alkylated products. This operationally simple methodology can introduce linear, branched, and cyclic alkyl chains, as well as a phenyl group, at the beta-carbon position. The key to this success was enhancement of the reactivity of alkenyl-heteroaromatic substrates via Lewis acid activation, in combination with the use of readily available and highly reactive Grignard reagents and a copper catalyst coordinated by a chiral chelating diphosphine ligand.
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