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Asymmetric Synthesis of (1‐Ferrocenylalkyl)amine and 1,1′‐Bis(1‐aminoalkyl)ferrocene Derivatives
Author(s) -
Enders Dieter,
Lochtman René
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199804)1998:4<689::aid-ejoc689>3.0.co;2-s
Subject(s) - chemistry , reagent , amine gas treating , nucleophile , medicinal chemistry , hydrazine (antidepressant) , enantiomer , bond cleavage , nucleophilic addition , ferrocene , hydrazone , cleavage (geology) , organic chemistry , stereochemistry , catalysis , electrochemistry , electrode , chromatography , geotechnical engineering , fracture (geology) , engineering
The aldehydes 1 and 5 were converted to the corresponding SAMP hydrazones 2 and 6 , respectively. Subsequent nucleophilic 1,2‐addition of organolithium reagents to the C−N double bonds and cleavage of the N−N hydrazine bond using an excess of BH 3 ·THF afforded (1‐ferrocenylalkyl)amines ( N ‐protection → 4 ) and 1,1′‐bis(1‐aminoalkyl)ferrocenes (N‐protection → 8 ) in good overall yields (32−88%), with very high enantiomeric excesses ( ee = 90−98%) and dl / meso ratios of up to 95:5.