Enantioselective Synthesis of Planar Chiral ortho-Functionalised Ferrocenylketones
- 31 December 1997
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 12 (12) , 1462-1464
- https://doi.org/10.1055/s-1997-1047
Abstract
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.Keywords
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