Development of a chemoenzymatic strategy for the synthesis of optically active and orthogonally protected polyamines |
| |
Authors: | Eduardo Busto Jose Montejo-Bernardo Vicente Gotor |
| |
Affiliation: | a Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Biotecnología de Asturias, Universidad de Oviedo, E-33071 Oviedo, Spain b Departamento de Química Física y Analítica, Universidad de Oviedo E-33071 Oviedo, Spain |
| |
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. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|