Enantioselective Synthesis of 1-Ferrocenylalkylamines via 1,2-Addition of Organolithium Compounds to Ferrocenecarboxaldehyde-SAMP-Hydrazone
- 1 February 1996
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1996 (02) , 126-128
- https://doi.org/10.1055/s-1996-5345
Abstract
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.Keywords
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