Institute of Crystallography - CNR

Synthesis, development and optimization of chemo-enzymatic, organ catalytic and enantioselective procedures for the preparation of chiral molecules) and active pharmaceutical compounds (APIs).

This research activity involves the development of “green” chemoenzymatic and organocatalytic methods for the preparation of chiral molecules and active pharmaceutical ingredients (APIs) that have a positive impact on the environment by reducing raw materials, waste and energy consumption.

The aim of the research activity is to develop new green methodologies for the preparation of chiral molecules and APIs which have a positive impact on the environment by reducing raw materials, waste and energy consumption. The research activity includes several sectors of organocatalysis: bi-functional catalysis, phase-transfer catalysis and NHC-carbenes. The research involves the optimization of enantioselective organ-catalytic procedures for the preparation of chiral sulphonic acids; the reaction has two main advantages, it works at room or low temperature and requires only a small excess of bisulfite. The use of phase-transfer catalysis produces cyclopropanes in high yields, complete diasteroselection and enantioselectivity. The reaction encompass the use of 4-nitro-5-styrylisoxazole, a class of compounds equivalent to cinnamates. The same type of catalysis was used for the synthesis of active pharmaceutical compounds (API) such as (S)-pregabalin and chiral gamma-amino acids. The research activity is also based on the design, preparation and characterization of new C-nucleoside analogues of the deoxyribose series containing bases modified in an anomeric position (β-diols, β-amino alcohols, etc.) for the development of artificial DNA as nano materials and catalysis.

Reference works

– Bencivenni G., Salazar Illera D., Moccia M., Houk K.N.,. Izzo J. A, Novacek J., Grieco P., J. M.Vetticatt, Waser M., Adamo M. F.A. Chemistry–A European Journal, 2021, 27, 11352-11366.
– Bencivenni G., Moccia M., Ravelli A., Gillick-Healy MW, Kelly B.G., Adamo M.F.A Organic & Biomolecular Chemistry, 2020, 18 (6), 1091-1094
– Moccia M., Cortigiani M., Monasterolo C., Torri F., Del Fiandra C., Fuller G., Kelly B., Adamo M. F.A. Organic Process Research & Development, 2015, 19, 1274-1281.
– Moccia M., Wells RJ, Adamo MFA. An improved procedure to prepare 3-methyl-4-nitroalkenethylisoxazoles and their reaction under catalytic enantioselective Michael addition. Organic & Biomolecular Chemistry, 2015, vol. 13; p. 2192-2195.

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