Organocatalytic Asymmetric Synthesis of Fluorinated Pyranopyrazoles

Abstract

An asymmetric fluorinated pyranopyrazoles were successfully constructed with good yield (up to 85%) and high enantioselectivity (up to 93% ee) via the reaction of unsaturated pyrazolones with α-trifluoromethyl β-fluorinated gem-diols. This method effectively avoids detrifluoroacetylation, furthermore, the absolute configuration of the products was unambiguously confirmed by Xray crystallographic analysis, providing reliable structural evidence for the asymmetric transformation.Pyranopyrazoles represent an important class of nitrogencontaining heterocyclic scaffolds that are widely found in natural products and pharmaceutical molecules (Figure 1). [1][2][3][4][5][6] Owing to their diverse bioactives, they hold broad application prospects in medicinal chemistry. The introduction of fluorine atoms typically leads to significant improvements in molecular in molecular properties such as metabolic stability, membrane 2 |