Organocatalytic Synthesis of γ-Amino Acid Precursors

Organocatalytic Synthesis of γ-Amino Acid Precursors via Masked Acetaldehyde under Micellar Catalysis: M. E. Casacchia, G. Giorgianni, E. Allegritti, L. Giansanti, A. Carlone, F. Pesciaioli
SynOpen 2023, 7, 29–32

Asymmetric synthesis via organocatalysis continues to attract a great deal of attention because of its efficacy, versatility, and user-friendliness. Recently, the groups of Professor Armando Carlone and Dr. Fabio Pesciaioli from the University of L’Aquila (Italy) reported a novel organocatalytic stereoselective approach to nitro precursors of γ-amino acids, which are important compounds in medicinal and biological chemistry.

Dr. Pesciaioli said: “In our first paper on the subject, we used masked acetaldehyde to effect an enantioselective addition to nitroalkenes. However, the best solvent proved to be chloroform and, therefore, we optimized the reaction in water via Design of Experiments (a chemometrics approach). In this case, however, despite the use of water, an ad-hoc organocatalyst was needed. Finally, combining supramolecular chemistry and organocatalysis we aimed at providing a solution for the synthesis of γ-amino acids precursors in water relying on a privileged catalyst and cost-effective surfactants. Moreover, we performed a NOESY study on the interaction between surfactants that are forming micelles and the reaction components and, in this regard, we hope that our contribution will be a source of inspiration in the field of micellar organocatalysis.”