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Herein we report a platinum-catalyzed isomerization of cyclopropenes to 1,3-dienes. Diverse dienylated alcohols were obtained in 42-98 % yield. The synthetic potential of the products was demonstrated by their use in Diels-Alder cycloadditions with various dienophiles. Isotope labelling studies provide strong support for a mechanism involving pericyclic [1,5]-σ-bond rearrangement of a vinyl platinum carbene intermediate.
Lindsey Eirika Kaelene Frederiksen
Anne-Clémence Corminboeuf, Matthew Wodrich, Rubén Laplaza Solanas, Shubhajit Das, Thanapat Worakul