Aqueous Flavin Photoredox Catalysis Drives Exclusive C3-Alkylation of Indolyl Radical Cations in Route to Unnatural Tryptophan Mimetics.
Org Lett
; 25(20): 3818-3822, 2023 May 26.
Article
em En
| MEDLINE
| ID: mdl-37191639
ABSTRACT
One way to build chemical diversity into indoles is to oxidize them to indolyl radical cations (Indâ¢+). These intermediates can accept new functional groups across C2-C3 bonds or independently at C2. Less encountered is selective diversification at C3, a position plagued by competing dearomative side reactions. We disclose an aqueous photoredox-catalyzed method for transforming Indâ¢+ into C3-substituted tryptophan mimetics that uses water as a transient protecting group to guide site-selective C3 alkylation.
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MEDLINE
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En
Ano de publicação:
2023
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Article