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Chiral cyclopentadienyl RhIII-catalyzed enantioselective cyclopropanation of electron-deficient olefins enable rapid access to UPF-648 and oxylipin natural products

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Abstract

Chiral cyclopentadienyl RhIII complexes efficiently catalyze enantioselective cyclopropanations of electron-deficient olefins with N-enoxysuccinimides as the C1 unit. Excellent asymmetric inductions and high diastereoselectivities can be obtained for a wide range of substrate combinations. The reaction proceeds under mild conditions without precautions to exclude air and water. Moreover, the synthetic utility of the developed method is demonstrated by concise syntheses of members of the oxylipin natural products family and the KMO inhibitor UPF-648.

Graphical abstract: Chiral cyclopentadienyl RhIII-catalyzed enantioselective cyclopropanation of electron-deficient olefins enable rapid access to UPF-648 and oxylipin natural products

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Publication details

The article was received on 20 Dec 2018, accepted on 15 Jan 2019 and first published on 17 Jan 2019


Article type: Edge Article
DOI: 10.1039/C8SC05702H
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    Chiral cyclopentadienyl RhIII-catalyzed enantioselective cyclopropanation of electron-deficient olefins enable rapid access to UPF-648 and oxylipin natural products

    C. Duchemin and N. Cramer, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC05702H

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