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Synthesis 2002(17): 2542-2560
DOI: 10.1055/s-2002-35628
PAPER
© Georg Thieme Verlag Stuttgart · New York

Diastereo- and Enantioselective Syntheses of C 2-Symmetric 1,n-Diamines by Nucleophilic Addition to Dialdehyde-SAMP-Hydrazones

Dieter Enders*, Michaela Meiers
Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany
Fax: +49(241)8092127; e-Mail: enders@rwth-aachen.de;
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Publication History

Received 6 August 2002
Publication Date:
20 November 2002 (online)

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Abstract

Different protected C 2-symmetric 1,n-diamines (R,R)- or (S,S)-4 and 8 can be prepared in high diastereo- and enantiomeric purity by nucleophilic 1,2-addition of organocerium reagents to the CN double bond of bis-SAMP-hydrazones (S,S)-2a∠c. The chiral starting materials are readily available by reaction of dialdehydes with the enantiopure hydrazine 1-amino-2-methoxymethylpyrrolidine (SAMP). Reductive NN bond cleavage of the hydrazines (R,R,S,S)- or (S,S,S,S)-3 and 7 afforded the title compounds (de 72∠98%, ee 96∠98%). The novel entry for the asymmetric synthesis of N-protected C 2-symmetric diamines presented here is highly flexible, as both the distance of the amino functions and the introduced residues R can be varied.

Key words

amines - hydrazones - nucleophilic additions - asym­metric synthesis - cerium