Electrochemical Iodine-Mediated Oxidation of Enamino-Esters to 2H-Azirine-2-Carboxylates supported by Design of Experiments.

Electrochemical Iodine-Mediated Oxidation of Enamino-Esters to 2H-Azirine-2-Carboxylates supported by Design of Experiments.
Chemistry. 2020 Mar 27;:
Authors: Hilt G, Babaoglu E
Abstract
An electrochemical iodine-mediated transformation of enamino-esters for the synthesis of 2 H -azirine-2-carboxylates is presented. In addition, a thermic conversion of azirines to 4-carboxy-oxazoles in quantitative yield without purification was described. Both classes 2 H -azirines-2-carboxylates and the 4-carboxy-oxazoles are substructures in natural products and therefore are of considerable interest for synthetic and pharmaceutical chemists. The optimization was not performed in a conventional manner with a one-factor-at-a-time process but with a Design of Experiments ( DoE ) approach. Beside a broad substrate scope the reaction was also employed to a robustness screen, a sensitivity assessment, and complemented with mechanistic considerations from cyclic voltammetry experiments.
PMID: 32220135 [PubMed - as supplied by publisher]

Source: Chemistry - March 26, 2020 Category: Chemistry Authors: Hilt G, Babaoglu E Tags: Chemistry Source Type: research