Iodine-Promoted Ring-Opening -Difunctionalization of Cyclopropanols with Enaminones: A Selective Route to 2,4-Diacylpyrroles.

In this work, we report a novel I-mediated ring-opening -difunctionalization of cyclopropyl alcohols with enaminones for the first time. The selective [3 + 2] annulation instead of [3 + 3] annulation under metal-free conditions enables a straightforward and efficient synthesis of structurally important 2,4-diacylpyrroles. Notably, this methodology dispenses with metal catalysts, proceeds under mild reaction conditions, and features not only simple operation but also suitability for gram-scale preparation and late-stage functionalization of complex bioactive molecules.

Ring-Opening α,β-Difunctionalization of Cyclopropanols with Azides Enables 4-Keto-Functionalized 1,2,3-Triazole Synthesis.

Selective C-C bond cleavage and transformation of organic small molecules to create products of increased value are one of the central goals in organic chemistry. In this study, we have developed a novel TEMPO-mediated ring-opening α,β-difunctionalization of cyclopropyl alcohols with organic azides to prepare structurally important 4-keto-1,2,3-triazoles under metal- and additive-free conditions. This protocol not only provides a straightforward and efficient method for the synthesis of 4-keto-functionalized 1,2,3-triazoles in one pot but also accomplishes the goal of constructing α,β-double C-N bonds via the ring opening of cyclopropyl alcohols for the first time.