Organocatalytic Enantioselective Synthesis of α‑Hydroxyketones through a Friedel–Crafts Reaction of Naphthols and Activated Phenols with Aryl- and Alkylglyoxal Hydrates

An efficient organocatalytic asymmetric synthesis of α-hydroxyketones has been developed. Quinine-derived thiourea catalyzed the enantioselective Friedel–Crafts alkylation of naphthols and activated phenols with aryl- and alkylglyoxal hydrates, providing the corresponding chiral α-hydroxyketones with high yields (up to 97%) and excellent enantioselectivities (up to 99% ee).

本研究已开发出一种高效的有机催化不对称合成α-羟基酮（α-hydroxyketones）的方法。以奎宁衍生硫脲（quinine-derived thiourea）为催化剂，可实现萘酚（naphthols）与活化酚（activated phenols）分别与芳基水合乙二醛、烷基水合乙二醛（aryl- and alkylglyoxal hydrates）的对映选择性傅克烷基化（enantioselective Friedel–Crafts alkylation）反应，最终得到相应的手性α-羟基酮产物，产率最高可达97%，对映选择性优异，最高达99% ee。