title: Decarboxylative Generation of 2-Azaallyl Anions: 2-Iminoalcohols via a Decarboxylative Erlenmeyer Reaction.
abstract: Condensation between the tetrabutylammonium salt of 2,2-diphenylglycine and aldehydes results in a decarboxylative Erlenmeyer reaction, affording 1,2-diaryl-2-iminoalcohols as a mixture of diastereomers in good yields. The diastereomeric ratio shifts over time, with the anti diastereomer and the syn oxazolidine tautomer serving as the kinetic and thermodynamic products, respectively. Addition of Lewis acids can catalyze the rates of reaction and product equilibration. The results highlight the stereochemical promiscuity of 1,2-diaryl-2-iminoalcohols in the presence of Lewis acids and Brønsted bases.
authors.forename: Shaojian
authors.initials: S
authors.lastname: Tang
authors.affiliation: ‡Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, United States.
authors.forename: Jong Yeun
authors.initials: JY
authors.lastname: Park
authors.affiliation: ‡Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, United States.
authors.forename: Andrew A
authors.initials: AA
authors.lastname: Yeagley
authors.affiliation: ‡Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, United States.
authors.forename: Michal
authors.initials: M
authors.lastname: Sabat
authors.forename: Jason J
authors.initials: JJ
authors.lastname: Chruma