title: Multicomponent Mannich reactions with boron enolates derived from diazo esters and 9-BBN.
abstract: Diazo esters, arylboranes, and carbamoyl imines undergo a 3-component Mannich condensation reaction. Catalyzed by Cu(II) salts, the reaction affords the corresponding isocyanate Mannich product: one that can be easily trapped in situ by other nucleophiles. The Mannich condensation corresponds to an α,α-disubstituted enolate addition to imines. The reaction was rendered asymmetric by using the (-)-phenylmenthol ester in good yield and selectivities.
authors.affiliation: Department of Chemistry, Center for Chemical Methodology and Library Development, Boston University, Boston, Massachusetts 02215, United States.
authors.forename: Yi
authors.initials: Y
authors.lastname: Luan
authors.forename: Scott E
authors.initials: SE
authors.lastname: Schaus
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001391:Azo Compounds; D001896:Boron Compounds; D004952:Esters; C004267:9-borabicyclo(3,3,1)nonane