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Synlett 1996; 1996(2): 126-128
DOI: 10.1055/s-1996-5345
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Enantioselective Synthesis of 1-Ferrocenylalkylamines via 1,2-Addition of Organolithium Compounds to Ferrocenecarboxaldehyde-SAMP-Hydrazone

Dieter Enders* , René Lochtman, Gerhard Raabe
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany
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Publication Date:
31 December 2000 (online)

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Nucleophilic 1,2-addition of organolithium compounds to ferrocenecarboxaldehyde-SAMP-hydrazone 2 leads to hydrazines 3 in almost quantitative yields and with virtually complete asymmetric induction (de ≥ 98%). Subsequent N-N bond cleavage via Raney-nickel promoted hydrogenolysis gives 1-ferrocenylalkylamines 4 in good overall yields (30-54%, 4 steps) and with high enantiomeric excesses (ee = 85-94%). The absolute configuration was determined by X-ray structure analysis of hydrazine (S,R)-3d.

1-ferrocenylalkylamines - asymmetric synthesis - SAMP-hydrazone - nucleophilic 1,2-addition - N-N bond cleavage

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