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

作者：Busto Eduardo; Gotor Fernandez Vicente^*; Montejo Bernardo Jose; Garcia Granda Santiago; Gotor Vicente

来源：Tetrahedron, 2009, 65(40): 8393-8401.

DOI：10.1016/j.tet.2009.08.001

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.

• 出版日期2009-10-3