Regio-and Enantioselective Catalytic Iodoalkoxylation of Styrene Derivatives with Unsaturated C3-Alcohols

The synthesis of unsaturated beta-iodoethers remains a significant challenge in modern organic chemistry. Three-component synthesis is a highly relevant approach for obtaining these compounds. The primary objective of this study was to develop a process where the triple bond of the reagent is preserved while iodine addition is selectively directed to the double bond of substituted styrenes. This work represents the first successful attempt to perform this reaction in an enantioselective manner. The iodoalkoxylation of substituted styrenes with unsaturated C-3-alcohols (propargyl and allyl) in the presence of diisopinocampheylborane leads to the formation of regioand enantiomerically enriched iodoethers with yields of 57-63%. The synthesized compounds were characterized by (H-1-NMR), (C-13-NMR) and FTIR spectroscopy. The synthesis followed established methodologies and proceeded without significant complications.