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Synlett 1997; 1997(4): 355-356
DOI: 10.1055/s-1997-5788
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Diastereo- and Enantioselective Synthesis of Protected 1,1'-Bis(1-aminoalkyl)ferrocenes via 1,2-Addition of Alkyllithium Compounds to Ferrocene-1,1'-dicarbaldehyde-bis-SAMP-Hydrazone

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

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Nucleophilic 1,2-additon of alkyllithium compounds to the ferrocene-1,1'-dicarbaldehyde-bis-SAMP-hydrazone (S,S)-2 leads to dihydrazines 3a-e in very good yields. Subsequent reductive N-N bond cleavage using BH3⋅THF gives protected 1,1'-bis(1-aminoalkyl)ferrocenes 4a-e in good overall yields (35-64%), with high enantiomeric excesses (ee=90-98%) and dl:meso ratios (up to 95:5).

1,1'-bis(1-aminoalkyl)ferrocenes - asymmetric synthesis - SAMP-hydrazone - nucleophilic 1,2-addition - N-N bond cleavage - C2-symmetric ligands

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