title: Stereoretentive Copper (II) Catalyzed Ritter Reactions of Secondary Cycloalkanols.
abstract: A Ritter-like coupling reaction of cyclic alcohols and both aryl and alkyl nitriles to form amides catalyzed by copper (II) triflate is described. These reactions proceed in good yields under mild and often solvent-free conditions. With 2- and 3-substituted cycloalkanols, amide products are formed with near complete retention of configuration. This is likely due to fast nucleophilic capture of a non-planar carbocations (hyperconjomers) stabilized by ring hyperconjugation. A critical aspect of this novel catalytic cycle is thein situactivation of the alcohol substrates by thionyl chloride to form chlorosulfites.
authors.affiliation: Department of Chemistry, Florida Atlantic University, 777 Glades Road, Boca Raton, Florida 33431.
authors.forename: Mohammed H
authors.initials: MH
authors.lastname: Al-Huniti
authors.affiliation: Department of Chemistry, Florida Atlantic University, 777 Glades Road, Boca Raton, Florida 33431.
authors.forename: Salvatore D
authors.initials: SD
authors.lastname: Lepore
keywords: Amides; Carbocations; Catalytic; Hyperconjomer; Ritter reaction; Stereoretentive