Browsing by Author "Wang, Dihuang 1991-"
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Item A Rhodium-Catalyzed [(4+2)+2] Cycloaddition of Allenediene for the Synthesis of Medium-Sized Rings(2018-08) Wang, Dihuang 1991-; Gilbertson, Scott R.; May, Jeremy A.; Do, Loi H.; Das, Joydip; Halasyamani, P. ShivThe synthesis of the compounds with medium-sized rings, especially those with a 5,8-fused ring system embedded into the structure, had long been pursued due to their ubiquitousness in numerous natural products and pharmaceutical molecules. These rings could be efficiently synthesized using metal-catalyzed higher order cycloaddition. In our studies, a previously-reported Rh-catalyzed [4+2+2] cycloaddition was developed and optimized to generate fused systems with a cyclooctadiene core from allenedienes and external alkynes. Upon screening of various metal complexes, ligands and solvents, a rhodium-BozPHOS complex was found to have the best reactivity. This cycloaddition between allenedienes and alkynes showed moderate yield and good substrate tolerance, showing good synthetic potential.