Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 8, Issue -, Pages 1333-1337Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.8.152
Keywords
Friedel-Crafts-type alkylation; laccase; one-pot reaction; organocatalysis; alpha-oxyamination; resin-supported peptide catalyst
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Funding
- Japan Society for the Promotion of Science [23750171]
- Grants-in-Aid for Scientific Research [23750171, 23550116, 24105506] Funding Source: KAKEN
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In the presence of a peptide catalyst and the oxidative enzyme laccase, a one-pot sequential reaction including a Friedel-Crafts-type alkylation of alpha,beta-unsaturated aldehydes followed by an alpha-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.
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