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GRAPHICAL ABSTRACT
ABSTRACT
A novel bifunctional organocatalysts library was developed as efficient tool for the stereoselective Michael addition of aldehydes with several aromatic nitroalkenes. Therefore, a phosphonic acid was used for the very first time as activating moiety in the field of organocatalysis. H-R-Pro-S-Pro-R-pAla-OMe (pAla stands for phosphonoalanine) was identified as the most effective one with up to 95:5 d.r. and 93:7 e.r over 12 GABA precursors examples. This catalyst was easily recycled and reused over 10 cycles without any significant loss of selectivity.
