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Radical addition of tetrahydrofuran to imines assisted by tert-butyl hydroperoxide

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Abstract The TBHP-promoted selective radical addition of tetrahydrofuran to imines resulting in β-amino ethers has been developed. The presented radical method of β-amino ether synthesis is based on initiation by… Click to show full abstract

Abstract The TBHP-promoted selective radical addition of tetrahydrofuran to imines resulting in β-amino ethers has been developed. The presented radical method of β-amino ether synthesis is based on initiation by available TBHP and does not require metal catalysis or light irradiation. Variety of β-amino ethers are formed in good to excellent yields, despite the possible side oxidation pathways: ether α-oxidation, the transformation of starting imines into amides, target β-amino ethers dehydrogenation.

Keywords: addition tetrahydrofuran; tetrahydrofuran imines; amino ethers; radical addition

Journal Title: Tetrahedron Letters
Year Published: 2020

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