Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 18, Pages 6239-6242Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600649
Keywords
asymmetric catalysis; chiral rhodium catalyst; cyclopropane; diazo derivatives; fluorine
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Funding
- INSA Rouen
- Rouen University
- CNRS
- EFRD
- Labex SynOrg [ANR-11-LABX-0029]
- Region Haute-Normandie (CrunchNetwork)
- IS:CE-Chem project
- Interreg IV: A France-(Channel)-England Program
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A catalytic asymmetric synthesis of halocyclopropanes is described. The developed method is based on a carbenoid cyclopropanation of 2-haloalkenes with tertbutyl alpha-cyano-alpha-diazoacetate using a chiral rhodium catalyst that permits access to a broad range of highly functionalized chiral halocyclopropanes (F, Cl, Br, and I) in good yields, moderate diastereoselectivity, and excellent enantiomeric ratios. The reported methodology represents the first general catalytic enantioselective approach to halocyclopropanes.
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