Studies On The Synthesis Of Highly Substituted Furans With Diazo Compounds By Metal Catalyzed

This thesis aims at the studies on the new method for synthesis of highly substituted furans with diazo compounds by transition-metal catalyzed, which mainly consists of the following parts:Part I: The Recent Progress of Diazo Compounds in Organic SynthesisThe review summarizes the development of diazo chemistry and focuses mainly on the progress that has been made very recently, particularly in the field of catalytic metal carbene derived fromα-diazo carbonyl compounds transformations. The recent progress of them in organic synthetic reactions, such as the X-H bond (e.g., C-H, O-H) insertion reaction, cyclopropanation reaction, and ylide reaction of diazo carbene, was summarized in details.Part II: Studies on the Synthesis of Highly Substituted Furans with Diazoacetates by transition-metal catalyzedWe have described the first examples of copper-catalyzed [4+1] cycloadditions ofα,β-acetylenic ketones withα-diazo esters. This new method furnished synthetically useful, highly substituted furan derivatives in a direct, one-flask process with good efficiency and regioselectivity. The protocol shows advantages in terms of its mild reaction condition simple operation, and easily available starting materials Furthermore, the reaction conditions and the scope of the process are examined, and a possible mechanism is proposed. All of the new compounds were characterized by not only NMR, and IR spectra, but also the single-crystal X-ray analysis in the case of the product 3aa.