Department of Chemistry, University of California, Berkeley, California 94720, USA.
J Am Chem Soc. 2013 Jan 30;135(4):1268-71. doi: 10.1021/ja311798q. Epub 2013 Jan 18.
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使得在 BINOL 衍生的磷酸盐的催化下，酚的直接和高对映选择性氟化去芳构化成为可能。该过程在环境反应条件下，高效地将简单易得的酚转化为具有反应性官能团的氟化手性小分子，对映选择性高。产物与研究充分的邻醌醇密切相关，为天然产物中用氟原子替代羟基的合成修饰提供了许多途径，也为生物等排体替换提供了令人兴奋的机会。
