PDF herunterladen
Synlett 1997; 1997(4): 355-356
DOI: 10.1055/s-1997-5788
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

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