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Development of a chemoenzymatic strategy for the synthesis of optically active and orthogonally protected polyamines

Author:
Busto García, Benjamín EduardoUniovi authority; Gotor Fernández, VicenteUniovi authority; Montejo Bernardo, José ManuelUniovi authority; García-Granda, SantiagoUniovi authority; Gotor Santamaría, Vicente MiguelUniovi authority
Publication date:
2009
Publisher version:
http://dx.doi.org/10.1016/j.tet.2009.08.001
Citación:
Tetrahedron, 65(40), P. 8393-8401 (2009); doi:10.1016/j.tet.2009.08.001
Descripción física:
p. 8393-8401
Abstract:

The chemical preparation and stereoselective enzymatic desymmetrization of a series of prochiral 2-substituted-1,3-propanediamines have been carried out using Pseudomonas cepacia lipase as biocatalyst. Syntheses of novel optically active orthogonally protected di- or triamines have been achieved for the first time with different grade of enantiodiscrimination depending on the C-2 substitution of the propane-1,3-diamine fragment. Final monoselective deprotection reactions of (S)-3-allyl-2-tert-butyl-1-(9-fluorenylmethyl)propane-1,2,3-triyltriscarbamate have allowed us to obtain a panel of novel enantiomerically enriched disubstituted triamines, compounds of difficult access by conventional synthetic methods.

The chemical preparation and stereoselective enzymatic desymmetrization of a series of prochiral 2-substituted-1,3-propanediamines have been carried out using Pseudomonas cepacia lipase as biocatalyst. Syntheses of novel optically active orthogonally protected di- or triamines have been achieved for the first time with different grade of enantiodiscrimination depending on the C-2 substitution of the propane-1,3-diamine fragment. Final monoselective deprotection reactions of (S)-3-allyl-2-tert-butyl-1-(9-fluorenylmethyl)propane-1,2,3-triyltriscarbamate have allowed us to obtain a panel of novel enantiomerically enriched disubstituted triamines, compounds of difficult access by conventional synthetic methods.

URI:
http://hdl.handle.net/10651/10818
ISSN:
0040-4020
Identificador local:

20090255

DOI:
10.1016/j.tet.2009.08.001
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