1621999-28-7Relevant articles and documents
Enantioselective copper-catalyzed carboetherification of unactivated alkenes
Bovino, Michael T.,Liwosz, Timothy W.,Kendel, Nicole E.,Miller, Yan,Tyminska, Nina,Zurek, Eva,Chemler, Sherry R.
supporting information, p. 6383 - 6387 (2014/06/24)
Chiral saturated oxygen heterocycles are important components of bioactive compounds. Cyclization of alcohols onto pendant alkenes is a direct route to their synthesis, but few catalytic enantioselective methods enabling cyclization onto unactivated alkenes exist. Herein reported is a highly efficient copper-catalyzed cyclization of γ-unsaturated pentenols which terminates in C-C bond formation, a net alkene carboetherification. Both intra- and intermolecular C-C bond formations are demonstrated, thus yielding functionalized chiral tetrahydrofurans as well as fused-ring and bridged-ring oxabicyclic products. Transition-state calculations support a cis-oxycupration stereochemistry-determining step.