10.1016/S0040-4039(00)99135-4
The study investigates the asymmetric alkylation of arylacetic acid derivatives using binaphthyl esters as chiral auxiliaries. The researchers, Kaoru Fuji and colleagues, focused on synthesizing optically active 2-arylalkanoic acids, which are important due to their biological activity. They used (R)-binaphthyl esters of substituted and unsubstituted phenylacetic acids and alkylated them with various alkylating agents such as isopropyl iodide and isobutyl iodide. The reactions were carried out in tetrahydrofuran (THF) with lithium diisopropylamide (LDA) and hexamethylphosphoric triamide (HMPA) as reagents. The study demonstrated high diastereoselectivity, with the bulkiness of the alkylating agents significantly influencing the stereoselectivity. The phenolic hydroxyl group in the binaphthyl esters was found to be crucial for achieving high diastereoselectivity. The researchers also explored the effects of different substituents and reaction conditions on the yield and diastereomeric ratios of the products. The study provides insights into the mechanism of the reaction and its potential applications in the synthesis of biologically active compounds.