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Please use this identifier to cite or link to this item: http://hdl.handle.net/10651/10818

Title: Development of a chemoenzymatic strategy for the synthesis of optically active and orthogonally protected polyamines
Author(s): Busto García, Benjamín Eduardo
Gotor Fernández, Vicente
Montejo Bernardo, José Manuel
García-Granda, Santiago
Gotor Santamaría, Vicente Miguel
Issue date: 2009
Publisher version: http://dx.doi.org/10.1016/j.tet.2009.08.001
Citation: Tetrahedron, 65(40), P. 8393-8401 (2009); doi:10.1016/j.tet.2009.08.001
Format extent: 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.
URI: http://hdl.handle.net/10651/10818
ISSN: 0040-4020
Local identifier: 20090255
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