4.8 Article

Organocatalysis in radical chemistry.: Enantioselective α-oxyamination of aldehydes

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 14, Pages 4124-+

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja069245n

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Funding

  1. NIGMS NIH HHS [R01 GM054656-10, R01 GM054656, R01 GM054656-09, P30 GM103332] Funding Source: Medline
  2. PHS HHS [NIGMS-54656] Funding Source: Medline

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We have developed an efficient radical alpha-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 alpha-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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