19822-12-9Relevant academic research and scientific papers
Templated carbene metathesis reactions from the modular assembly of enol-diazo compounds and propargyl acetates
Qian, Yu,Shanahan, Charles S.,Doyle, Michael P.
, p. 6032 - 6037 (2013/09/24)
A Lewis acid mediated coupling reaction of enol-diazo nucleophiles and propargyl acetates has provided rapid and diverse access to complex alkynyl-tethered diazocarbonyl compounds. The ability of the coupling reaction to vary critical functionality flanking the diazo group was explored as a way to direct the outcome of a series of metal-catalyzed carbene metathesis cascade reactions. These cascade reactions provided diverse, biologically interesting carbocyclic and heterocyclic compounds in only a few steps from readily available materials. A general coupling strategy for the formation of alkynyl-substituted diazocarbonyl templates for catalytic cascade reactions is described. With the synthetic flexibility imparted to the coupling process and the facile cyclization of the first-formed metal carbene to secondary vinyl carbene templates, selective ylide, C-H insertion, and atom-transfer processes provide directed functionalization in cyclic compounds.
