2007Journal of the American Chemical SocietyOpen access

Organocatalysis in Radical Chemistry. Enantioselective α-Oxyamination of Aldehydes

Mukund P. Sibi, Masayuki Hasegawa

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Abstract

We have developed an efficient radical α-oxyamination reaction using chiral organocatalysts. The reaction can be carried out with inexpensive SET reagents, and a reasonably broad substrate scope has been established. Good to high enantioselectivity for the α-oxygenated products are obtained using 20 mol % of the catalyst. The methodology reported in this work adds to the repertoire of asymmetric radical reactions that can be conducted using organocatalysts.

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What this paper is about

We have developed an efficient radical α-oxyamination reaction using chiral organocatalysts. The reaction can be carried out with inexpensive SET reagents, and a reasonably broad substrate scope has been established. Good to high enantioselectivity for the α-oxygenated products are obtained using 20 mol % of the catalyst. The methodology reported in this work adds to the repertoire of asymmetric radical reactions that can be conducted using organocatalysts.

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Available abstract

We have developed an efficient radical α-oxyamination reaction using chiral organocatalysts. The reaction can be carried out with inexpensive SET reagents, and a reasonably broad substrate scope has been established. Good to high enantioselectivity for the α-oxygenated products are obtained using 20 mol % of the catalyst. The methodology reported in this work adds to the repertoire of asymmetric radical reactions that can be conducted using organocatalysts.

Key concepts: Chemistry, Enantioselective synthesis, Organocatalysis, Scope (computer science), Reagent, Substrate (aquarium), Catalysis, Radical

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