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Synlett 1997; 1997(12): 1462-1464
DOI: 10.1055/s-1997-1047
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Enantioselective Synthesis of Planar Chiral ortho-Functionalised Ferrocenylketones

Dieter Enders* , René Peters, René Lochtman, Jan Runsink
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany, Fax: Int. +241/8888-127; E-mail: Enders@RWTH-Aachen.de
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Publikationsdatum:
31. Dezember 2000 (online)

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An efficient and flexible asymmetric synthesis of planar chiral ortho-functionalised ferrocenylketones 4a-f in good overall yields (47-55%) and enantiomeric excesses (ee=71,90-96%) is described. Key step of the procedure is the diastereoselective (de=95-98%) ortho-metalation of benzoylferrocene-SAMP-hydrazone 2, followed by trapping with various electrophiles such as MeI, Me3SiCl, Ph2PCl / BH3•THF, Ph2CO, DMF and I2. Subsequent oxidative (O3) or reductive [Sn(II) or Ti(III)] hydrazone cleavage leads to the title compounds.

planar chirality - diastereoselective ortho-metalation - ferrocenylketones - asymmetric synthesis - SAMP-hydrazones