Efficient Approaches for the Synthesis of Diverse α-Diazo Amides

Abstract

Metal-catalysed carbenoid chemistry can be exploited for the synthesis of diverse ranges of small molecules from α-diazo carbonyl compounds. In this paper, three synthetic approaches to α-diazo amides are described, and their scope and limitations are determined. On the basis of these synthetic studies, recommendations are provided to assist the selection of the most appropriate approach for specific classes of product. The availability of practical and efficient syntheses of diverse α-diazo acetamides is expected to facilitate the discovery of many different classes of bioactive small molecules.

Iridium(III)-Catalyzed C–H Cyclization of Sulfoximines with Diazo Meldrum’s Acids for the Synthesis of Cyclic Sulfoximines

“…Commercially available reagents were used without purification [ 7a (Alfa Aesar), 7b (TCI), 7c (TCI), 7d (TCI), 7e (Aldrich), 9a (Alfa Aesar), 9b (TCI), 9c (Alfa Aesar), 9d (Alfa Aesar), and 9e (Alfa Aesar)]. Sulfoximines ( 1 ) and diazo Meldrum’s acid ( 2 ) were prepared by the reported method . All reaction mixtures were stirred magnetically and monitored by thin-layer chromatography using silica gel precoated glass plates, which were visualized with ultraviolet light, and then developed using a solution of KMnO 4 .…”