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Synlett 2001; 2001(1): 0029-0032
DOI: 10.1055/s-2001-9693
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A Simple and very Efficient Route to New Chiral Ferrocenyl Diamines via Diastereoselective Alkylation

Olivier Delacroix* , Sophie Picart-Goetgheluck, Lucien Maciejewski, Jacques Brocard, Guy Nowogrocki
  • *Laboratoire de Catalyse de Lille associé au CNRS, Groupe de Synthèse Organométallique, ENSCL, Cité Scientifique, BP 108, F-59652 Villeneuve d'Ascq Cedex, France; Fax +33(0)3 20 43 65 85; E-mail: sophie.goetgheluck@ensc-lille.fr
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Publication Date:
31 December 2001 (online)

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A new family of chiral ferrocenyl diamines bearing one planar chirality and one or two stereogenic centers has been easily synthesized starting from 2-(N,N-dimethylaminomethyl)ferrocenylcarboxaldehyde (1) via a highly diastereoselective step. All diamines were obtained in high diastereomeric excesses and optical purities (de and ee >98%) and in 80% to 85% yields.

diamines - diastereoselectivity - N,N-dimethylaminomethylferrocene - imines - organometallic reagents