Chiral Anion Phase-Transfer Catalysis Applied to the Direct Enantioselective Fluorinative Dearomatization of Phenols

Chiral anion phase-transfer catalysis has enabled the direct and highly enantioselective fluorinative dearomatization of phenols catalyzed by a BINOL-derived phosphate. The process efficiently transforms simple, readily available phenols into fluorinated chiral small molecules bearing reactive functionality under ambient reaction conditions with high enantioselectivity. The close relationship of the products with well-studied o-quinols provides numerous avenues for synthetic elaboration and exciting opportunities for bioisosteric replacement of hydroxyl with fluorine in natural products.手性阴离子相转移催化（Chiral anion phase-transfer catalysis）已成功实现由联萘酚衍生的磷酸酯（BINOL-derived phosphate）催化的直接、高对映选择性苯酚氟化脱芳构化反应。该过程可在温和反应条件下，以优异的对映选择性，将简单易得的苯酚高效转化为带有反应性功能基团的手性氟化小分子。产物与研究充分的邻醌醇（o-quinols）结构密切相关，可为合成衍生化提供众多可行路径，同时也为天然产物中以氟原子生物等排置换羟基（bioisosteric replacement）带来了令人振奋的应用机遇。