Copper-Catalyzed Enantioselective Hydroalkoxylation of Alkenols for the Synthesis of Cyclic Ethers
Dake Chen, Ilyas A. Berhane, Sherry R. Chemler
Abstract
The copper-catalyzed enantioselective intramolecular hydroalkoxylation of unactivated alkenes for the synthesis of tetrahydrofurans, phthalans, isochromans, and morpholines from 4- and 5-alkenols is reported. The substrate scope is complementary to existing enantioselective alkene hydroalkoxylations and is broad with respect to substrate backbone and alkene substitution. The asymmetric induction and isotopic labeling studies support a polar/radical mechanism involving enantioselective oxycupration followed by C-[Cu] homolysis and hydrogen atom transfer. Synthesis of the antifungal insecticide furametpyr was accomplished.
Topics & Concepts
Enantioselective synthesisChemistryAlkeneIntramolecular forceCatalysisHomolysisSubstrate (aquarium)Combinatorial chemistryStereochemistryOrganic chemistryMedicinal chemistryRadicalOceanographyGeologyOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsVanadium and Halogenation Chemistry