Double Catalytic Kinetic Resolution via Substractive Horeau Amplification in the Confined Spaces of TAMO

Categorías: IN2UB

Highlighted paper from Homogeneous Catalysis group. The homochiral metal-organic framework TAMOF-1 was used as a heterogeneous catalyst in the kinetic resolution of styrene oxide by ring opening reactions with a set of anilines yielding secondary amino alcohols. The linear products arising from the attack on the non-benzylic position of styrene oxide underwent a second kinetic resolution by reacting with the epoxide, resulting in an amplification of its final enantiomeric excess and a concomitant formation of an array of isomeric aminodiols (substractive Horeau amplification effect). Computational studies rationalized the experimental results, providing a deep understanding of the whole process involving the two successive kinetic resolutions. These studies have revealed that TAMOF-1 lowered the reaction barriers of all ring opening processes taking place inside channels.

Differentiation of Epoxide Enantiomers in the Confined Spaces of an Homochiral Cu(II) Metal-Organic Framework by Kinetic Resolution. J. Cabezas-Giménez, V. Lillo, J.L. Núñez-Rico, M.N. Corella-Ochoa, J. Jover, J.R. Galán-Mascarós, A. Vidal-Ferran. Chemistry – A European Journal, June 2021.