Synthesis of chiral α-hydroxy acids via palladium-catalyzed C(sp3)–H alkylation of lactic acid

Abstract

Herein we report a Pd-catalyzed alkylation of lactic acid with the assistance of 8-aminoquinoline auxiliary. A wide range of alkyl iodides bearing β-hydrogen atoms are compatible with the reaction conditions, providing a practical and straightforward alternative to access chiral α-hydroxy acids (AHAs). The new reactions have been applied for the synthesis of isotope-labeled AHAs and a sugar-containing complex AHA.