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Asymmetric one-pot sequential Friedel-Crafts-type alkylation and ?-oxyamination catalyzed by a peptide and an enzyme.

ABSTRACT: In the presence of a peptide catalyst and the oxidative enzyme laccase, a one-pot sequential reaction including a Friedel-Crafts-type alkylation of ?,?-unsaturated aldehydes followed by an ?-oxyamination was realized. The reaction in aqueous solvent to promote the enzymatic oxidation, and the use of a peptide catalyst compatible with such conditions, were essential. The present sequential reaction afforded oxygen-functionalized indole or pyrrole derivatives in a highly enantioselective manner.

SUBMITTER: Akagawa K

PROVIDER: S-EPMC3458757 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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Asymmetric one-pot sequential Friedel-Crafts-type alkylation and α-oxyamination catalyzed by a peptide and an enzyme.

Akagawa Kengo K Umezawa Ryota R Kudo Kazuaki K

Beilstein journal of organic chemistry 20120817

In the presence of a peptide catalyst and the oxidative enzyme laccase, a one-pot sequential reaction including a Friedel-Crafts-type alkylation of α,β-unsaturated aldehydes followed by an α-oxyamination was realized. The reaction in aqueous solvent to promote the enzymatic oxidation, and the use of a peptide catalyst compatible with such conditions, were essential. The present sequential reaction afforded oxygen-functionalized indole or pyrrole derivatives in a highly enantioselective manner. ...[more]

PMID: 23019467

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