284474-43-7Relevant academic research and scientific papers
Gold-catalyzed diastereoselective cycloisomerization of alkylidene-cyclopropane-bearing 1,6-diynes
Zheng, Hongchao,Adduci, Laura L.,Felix, Ryan J.,Gagne, Michel R.
supporting information, p. 7904 - 7907 (2014/08/05)
An unprecedented gold-catalyzed diastereoselective cycloisomerization of 1,6-diynes bearing an alkylidene cyclopropane moiety has been developed. This methodology enables rapid access to a variety of 1,2-trimethylenenorbornanes, which are important building blocks in the preparations of abiotic and sesquiterpene core structures. When gold met alkylidenecyclopropane: Cationic gold catalysts can mediate the highly exothermic (≈60 kcal mol-1) cycloisomerization of 1,6-diynes bearing an alkylidene cyclopropane moiety. This diastereoselective methodology efficiently generates 1,2- trimethylenenorbornanes, an important building block for abiotic targets and sesquiterpene natural products. DCE=1,2-dichloroethane, Tf= trifluoromethanesulfonyl, Tol=Tolyl.
