Synthesis of phosphoenol pyruvates. Theoretical and experimental study

摘要

A theoretical and experimental study of the reaction of alpha-chloropyruvate with trialkyl phosphites in toluene is reported. The phosphoenol pyruvate obtained was characterized by (H-1, C-13 and P-31) NMR. DFT-based reactivity descriptors are used to explain the main reaction product found experimentally. Global and local reactivity indices, namely global electrophilicity and Parr function, were computed at the B3LYP/6-311(d) level of theory. The solvent's effect on the reactivity indices is elucidated. The computed regioselectivity is in good agreement with experimental outcomes. (C) 2014 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.