Synthesis of Novel C ₂ Bishydroxamic Acid Ligands and their Application in Asymmetric Epoxidation Reactions

Dedicated to Professor Hisashi Yamamoto for his 80th birthday

Abstract

Asymmetric oxidation reactions have significantly benefited from bishydroxamic Brønsted acid ligands, and they can proceed with remarkable stereoselectivity. Designing and synthesizing these ligands are essential for achieving high enantioselectivity in metal-catalyzed oxidation reactions. This paper presents a straightforward method for synthesizing novel phenyl-ring-centric bishydroxamic acids (BHA). A preliminary analysis of Ti-BHA-catalyzed reactions resulted in asymmetric epoxides with an exceptional enantiomeric excess (>99% ee). At the same time, ongoing experiments aim to improve the reaction conversion for enhanced overall efficiency.

Key words

enantioselective catalysis - asymmetric epoxidation - chiral bis-hydroxamic acid - C ₂-symmetric ligand - metal-catalyzed oxidation reactions

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