ISSN:
1434-193X
Keywords:
Ferrocene
;
Asymmetric synthesis
;
Nucleophilic 1,2-addition
;
Hydrazones
;
Cleavage reactions
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 BH3·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.
Type of Medium:
Electronic Resource
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