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Multicomponent versus domino reactions: One-pot free-radical synthesis of ?-amino-ethers and ?-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 ?-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.

SUBMITTER: Rossi B

PROVIDER: S-EPMC4311587 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols.

Rossi Bianca B Pastori Nadia N Prosperini Simona S Punta Carlo C

Beilstein journal of organic chemistry 20150115

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. Th ...[more]

PMID: 25670994

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