A Stereoselective entry into functionalized 1,2-diamines by zinc-mediated homologation of α-aminoacids

Organic Letters

Volumn 9, Issue 13, 2007, Pages 2521-2524

  Hoang, Cam Thuy ^a   Alezra, Valérie ^a   Guillot, Régis ^a   Kouklovsky, Cyrille ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; DIAMINE; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

AMINO ACIDS; DIAMINES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ZINC;

EID: 34547198945     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0708020     Document Type: Article

References (25)

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16. The whole synthetic sequence was performed on both racemic and enantiomerically pure material for each amino acid. The enantiomeric purity of each intermediate was checked by HPLC on a chiral column.
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19. Tetrabutylammonium cyanoborohydride or sodium triacetoxyborohydride did not improve the stereoselectivity.
20. Reviews: (a) Venturello, P.; Barbero, M. Science of Synthesis; Georg Thieme Verlag: Stuttgart, 2005; Vol., 8b, p 881.
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22. To the best of our knowledge, there is only one example of reduction of an enaminoester derivative under Birch conditions: Schlessinger, R. H.; Iwanowicz, E. J.; Springer, J. P. J. Org. Chem. 1986, 51, 3070.
23. The presence of alcohol 9a-d must be due to traces of moisture in the reaction medium.
24. For a discussion about the stereoselectivity of the Birch reduction: Pradhan, S. K. Tetrahedron 1986, 42, 6351.
25. 13C NMR spectra of compounds 8a-e and minor isomers for compounds 6a and 6e allowed cis/trans assignment for each isomer in compounds 6a-e (see Supporting Information for details).