Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 16, Pages 5447-5451Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201814453
Keywords
asymmetric catalysis; cobalt; cooperative catalysis; diastereodivergency; hydrogen bonds
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Funding
- Deutsche Forschungsgemeinschaft [PE 818/7-1, 310990893]
- state of Baden-Wurttemberg through bwHPC
- German Research Foundation (DFG) [INST 40/467-1 FUGG]
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Achieving enzyme-like catalytic activity and stereoselectivity without the typically high substrate specificity of enzymes is a challenge in the development of artificial catalysts for asymmetric synthesis. Polyfimctional catalysts are considered to be a promising tool for achieving excellent catalytic efficiency. A polyfunctional catalyst system was developed, which incorporates two Lewis acidic/BrOnsted basic cobalt centers in combination with triazolium moieties that are crucial for high reactivity and excellent stereoselectivity in the direct 1,4-addition of oxindoles to maleimides. The catalyst is assembled through click chemistry and is readily recyclable through precipitation by making use of its charges. Kinetic studies support a cooperative mode of action. Diastereodivergency is achievable with either Roc-protected or unprotected maleimide.
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