Allylic C–H functionalization reactions for the cyclization of hemisilaketals

Abstract

Polyhydroxylated compounds are among the most valued in organic chemistry due to their biological activity and, consequently, their pharmaceutical potential. 1,3-Diols are structural motifs commonly found in therapeutically significant drugs, such as statins. Therefore, the development and optimization of efficient synthetic methods to obtain them represent an important challenge. This is a constantly evolving field of research among other reasons, due to the difficulty in achieving stereoselectivity. This project focuses on the synthesis of these valuable moieties based on allylic C–H activation, a less studied strategy for C–O bond formation. The formation of hemisilaketals leads to silaketals through a rhodium-catalyzed cyclization. Finally, a deprotection step is required to obtain stereoselective syn-1,3-diols, as depicted in the general scheme below. The synthesis and characterization of syn-1,3-diols has been accomplished from various substrates. This project also reports modifications to the synthetic pathway that enhance efficiency and yield higher-purity products. The methodology has been established as an effective and reproducible route for the stereoselective synthesis of the desired compounds. Furthermore, the range of possibilities for accessing these valuable compounds has been expanded, offering an alternative approach.