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Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters.

ABSTRACT: The synergistic use of chiral bifunctional ammonium iodide catalysts in combination with simple catalytically relevant aldimines allows for an unprecedented asymmetric α-hydroxylation reaction of β-ketoesters using H₂O₂. The reaction proceeds via in situ formation of a hypervalent iodine species, which then reacts with the used aldimine to generate an activated electrophilic oxygen transfer reagent.

SUBMITTER: Mairhofer C

PROVIDER: S-EPMC7418104 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Synergistic Ammonium (Hypo)Iodite/Imine Catalysis for the Asymmetric α-Hydroxylation of β-Ketoesters.

Mairhofer Christopher C Novacek Johanna J Waser Mario M

Organic letters 20200724 15

The synergistic use of chiral bifunctional ammonium iodide catalysts in combination with simple catalytically relevant aldimines allows for an unprecedented asymmetric α-hydroxylation reaction of β-ketoesters using H<sub>2</sub>O<sub>2</sub>. The reaction proceeds via in situ formation of a hypervalent iodine species, which then reacts with the used aldimine to generate an activated electrophilic oxygen transfer reagent. ...[more]

PMID: 32706973

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