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）已实现由联萘酚（BINOL）衍生的磷酸酯催化的苯酚直接且高对映选择性氟化脱芳构化反应。该过程可在室温反应条件下，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氟化手性小分子。该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多样途径，同时也为天然产物中羟基的氟代生物电子等排体替换带来了极具前景的应用机会。