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

Autor:	Dieter Enders, Michaela Meiers
Rok vydání:	2002
Předmět:	chemistry.chemical_classification Nucleophilic addition Double bond Chemistry Organic Chemistry Hydrazine Enantioselective synthesis Medicinal chemistry Catalysis chemistry.chemical_compound Enantiopure drug Nucleophile Enantiomer Bond cleavage
Zdroj:	Synthesis. :2542-2560
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-2002-35628
Popis:	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.
Databáze:	OpenAIRE
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