Synthesis of Optically Active beta- or gamma-Alkyl-Substituted Alcohols through Copper-Catalyzed Asymmetric Allylic Alkylation with Organolithium Reagents

An efficient one-pot synthesis of optically active beta-alkyl-substituted alcohols through a tandem copper-catalyzed asymmetric allylic alkylation (AAA) with organolithium reagents and reductive ozonolysis is presented. Furthermore, hydroboration-oxidation following the Cu-catalyzed AAA leads to the corresponding homochiral gamma-alkyl-substituted alcohols.