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

Beilstein Journal of Organic Chemistry

Kengo Akagawa¹  Kazuaki Kudo¹  Ryota Umezawa¹ 

[1] Institute of Industrial Science, University of Tokyo, 4-6-1 Komaba, Meguro-ku, Tokyo 153-8505, Japan;

关键词: Friedel–Crafts-type alkylation;    laccase;    one-pot reaction;    organocatalysis;    α-oxyamination;    resin-supported peptide catalyst;   

DOI  :  10.3762/bjoc.8.152

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown