Hydrogen-Bonded Matched Ion Pair Gold(I) Catalysis
Àlex Martí, Gala Ogalla, Antonio M. Echavarren
Abstract
High Resolution Image Download MS PowerPoint Slide The enantioselective reaction of 1,6-enynes with O -, N -, and C -nucleophiles has been developed by matched ion pair gold(I) catalysis in which the chiral gold(I) cation and anion are H-bonded through a urea group. Very high levels of enantiocontrol are achieved (up to >99:1 er) for a broad scope of substrates. DFT studies demonstrate the importance of the H-bond donor group in anchoring the matched chiral cation- and anion-favoring additional noncovalent interactions.
Topics & Concepts
CatalysisEnantioselective synthesisNucleophileChemistryHydrogen bondIonCombinatorial chemistryOrganocatalysisNon-covalent interactionsStereochemistryOrganic chemistryMoleculeCatalytic Alkyne ReactionsSynthetic Organic Chemistry MethodsAsymmetric Synthesis and Catalysis