title: Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols.
abstract: Following an optimized multicomponent procedure, an aryl amine, a ketone, and a cyclic ether or an alcohol molecule are assembled in a one-pot synthesis by nucleophilic radical addition of ketyl radicals to ketimines generated in situ. The reaction occurs under mild conditions by mediation of the TiCl4/Zn/t-BuOOH system, leading to the formation of quaternary β-amino-ethers and -alcohols. The new reaction conditions guarantee good selectivity by preventing the formation of secondary products. The secondary products are possibly derived from a competitive domino reaction, which involves further oxidation of the ketyl radicals.
authors: Department of Chemistry, Materials, and Chemical Engineering "G. Natta" - Politecnico di Milano, Via Leonardo da Vinci 32, I-20131 Milano, Italy; Fax (+39)0223993180.
authors: Bianca
authors: B
authors: Rossi
authors: Department of Chemistry, Materials, and Chemical Engineering "G. Natta" - Politecnico di Milano, Via Leonardo da Vinci 32, I-20131 Milano, Italy; Fax (+39)0223993180.
authors: Nadia
authors: N
authors: Pastori
authors: Department of Chemistry, Materials, and Chemical Engineering "G. Natta" - Politecnico di Milano, Via Leonardo da Vinci 32, I-20131 Milano, Italy; Fax (+39)0223993180.
authors: Simona
authors: S
authors: Prosperini
authors: Department of Chemistry, Materials, and Chemical Engineering "G. Natta" - Politecnico di Milano, Via Leonardo da Vinci 32, I-20131 Milano, Italy; Fax (+39)0223993180.
authors: Carlo
authors: C
authors: Punta
keywords: aminoalcohols; free-radical addition; imine; multicomponent reaction; titanium salts