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

Chem Sci

Laboratory of Asymmetric Catalysis and Synthesis , EPFL SB ISIC LCSA , BCH 4305 , CH-1015 Lausanne , Switzerland . Email:

Published: March 2019

Chiral cyclopentadienyl Rh complexes efficiently catalyze enantioselective cyclopropanations of electron-deficient olefins with -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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6419935PMC
http://dx.doi.org/10.1039/c8sc05702hDOI Listing

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