Brønsted Acid‐Catalyzed Enantioselective Iodocycloetherification Enabled by Triphenylphosphine Selenide Cocatalysis
Sudip Guria, Constantin G. Daniliuc, Ulrich Hennecke
Abstract
Abstract Enantioselective iodocycloetherifications can be conducted using sterically highly demanding BINOL‐based phosphoric acid diesters as catalyst. To achieve highly enantioselective reactions, cocatalysis by triphenylphosphine selenide is necessary. With cocatalysis, good to excellent enantioselectivities can be achieved for a broad range of substrates using catalyst and cocatalyst loadings as low as 1 mol %. The triphenylphosphine selenide cocatalyst itself does not strongly influence diastereoselectivity, but leads to higher reactivity and, in combination with a BINOL‐based phosphoric acid diester, to good enantioselectivity. magnified image
Topics & Concepts
Enantioselective synthesisChemistrySelenideTriphenylphosphinePhosphoric acidSteric effectsCatalysisTriphenylphosphine oxideReactivity (psychology)Organic chemistryCombinatorial chemistryMedicinePathologyAlternative medicineSeleniumVanadium and Halogenation ChemistryAlkaloids: synthesis and pharmacologyOxidative Organic Chemistry Reactions