Combining Q2MM modeling and kinetic studies for refinement of the osmium-catalyzed asymmetric dihydroxylation (AD) mnemonic

The interactions between the substrate and the ligand in the Sharpless AD reaction have been examined in detail, using a combination of substrate competition experiments and molecular modeling of transition states. There is a good agreement between computational and experimental results, in particular for the stereoselectivity of the reaction. The influence of each moiety in the second-generation ligand (DHQD)2PHAL on the rate and selectivity of the reaction has been elucidated in detail.

The role of each moiety of one of the most popular ligands in the Sharpless AD reaction has been elucidated in detail using a combination of kinetic and computational studies.Figure optionsDownload as PowerPoint slide