A new approach to diastereoselective and enantioselective cyclopropane syntheses using the chiral iron carbene complexes S- and R-[η5- C5H5)(CO)2Fe=CH[η6-o-CH3OC6H4)CR(CO)3]]+

Qinwei Wang, Michael F. Mayer, Courtney Brennan, Fukang Yang, M. Mahmun Hossain, Desiree S. Grubisha, Dennis Bennett

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Different methods for the synthesis of iron carbene complexes or their precursors have been summarized. New diastereomerically pure carbene precursors RR-(+)- and SS-(-)-(η5-C5H5)(CO)2FeCH(OSiMe3)[η6-o- CH3OC6H4Cr(CO)3] have been prepared by the reaction of the Fp anion with enantiomerically pure S-(+) or R-(-)-o-anisaldehyde(tricarbonyl)chromium complexes. They were then converted to the corresponding iron carbene complexes S- and R-[η5-C5H5)(CO)2Fe=CH[η6-o-CH3OC6H4)Cr(CO)3]]+. Enantioselective carbene transfers from these complexes to 2-methylpropene, 1,1-diphenylethylene, styrene, p-methylstyrene, p-chlorostyrene, and p- trifluoromethylstyrene gave o-methoxyphenylcyclopropanes with high diastereoselectivities and moderate to excellent enantioselectivities. (C) 2000 Published by Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)4881-4891
Number of pages11
JournalTetrahedron
Volume56
Issue number28
DOIs
StatePublished - Jul 7 2000

Keywords

  • Alkene
  • Bimetallics
  • Carbenes
  • Cyclopropanation
  • Enantioselection

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