Described herein is a strategy for preparing 3° and 4° carbon-containing 3-alkylquinolones: molecules previously inaccessible and/or underexplored in synthetic- and medicinal chemistry. It was found that ~equimolar amounts of 4-(arylsulfonyl) quinolones and 2° allyl alcohols can react via nucleophilic aromatic substitution and allyl quinolyl ether Claisen rearrangement to yield the targeted quinolones. Key findings are fundamental and applied, including optimization of conditions and substrate for mild and high yielding [3,3] rearrangement, transition state analysis and enantiospecificity of the [3,3] step, and scope and limitations for the sequence. The work culminates in the synthesis of unique and previously unexplored antiparasitic endochin-like quinolones (ELQs) bearing 4°-carbons.