An easy and affordable route for obtaining chiral beta-aminated- and alpha,beta-diaminated aldehydes, 1,3-aminoalcohols, and related compounds by using organocatalysis is presented. The chiral secondary amine (S)-2-[bis(3,5-bistrifluoromethylphenyl)trimethylsilanyloxymethyl]pyrrolidine is used as the catalyst to activate alpha,beta-unsaturated aldehydes, which allows succinimide to add in a 1,4-regio- and stereoselective fashion thereby forming N-protected 1,3-aminoaldehydes in good yields and enantioselectivities. This is followed by two easy transformations giving rise to optically active 1,3-aminoalcohols, a common motif in many biologically active compounds, for example, fibrinogen receptor antagonists. Furthermore, optically active alpha,beta-syn-diaminated aldehydes were obtained by the addition of diethyl azodicarboxylate in a one-pot reaction.
A general synthesis of optically active gamma-butyrolactone autoregulators is developed by a two-step sequence to assemble 2,3-trans-disubstituted butyrolactones in high yields and enantioselectivities; the scope of this reaction was elaborated by setting up a library of alkyl-substituted butyrolactones and the synthesis of the autoregulators IM-2 and VB-D.
Other bioactive products U 1300A Modular and Organocatalytic Approach to γ-Butyrolactone Autoregulators from Streptomycetes. -A general synthesis of enantiopure γ-butyrolactone autoregulators is developed by a two-step sequence to assemble 2,3-trans-disubstituted butyrolactones (IV) in good yields and enantioselectivities. The approach is used to synthesize the autoregulators IM-2 (VI) and VB-D. The latter is obtained similarly to (VI) using the enantiomeric catalyst. -(ELSNER, P.; JIANG, H.; NIELSEN, J. B.; PASI, F.; JOERGENSEN*, K. A.; Chem. Commun. (Cambridge) 2008, 44, 5827-5829; Dep. Chem., Univ. Aarhus, DK-8000 Aarhus, Den.; Eng.) -M. Paetzel
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