Enantioselective oxygenation of exocyclic methylene groups by a manganese porphyrin catalyst with a chiral recognition site†

Autor:	Finn Burg, Christian Jandl, Stefan Breitenlechner, Thorsten Bach
Jazyk:	angličtina
Rok vydání:	2020
Předmět:	Hydrogen bond Enantioselective synthesis chemistry.chemical_element General Chemistry Combinatorial chemistry Oxygen ddc Catalysis Hydroxylation chemistry.chemical_compound Chemistry chemistry Yield (chemistry) Organic synthesis Methylene
Zdroj:	Chemical Science
ISSN:	2041-6539 2041-6520
Popis:	The natural enzyme cytochrome P450 is widely recognised for its unique ability to catalyse highly selective oxygen insertion reactions into unactivated C–H bonds under mild conditions. Its exceptional potential for organic synthesis served as an inspiration for the presented biomimetic hydroxylation approach. Via a remote hydrogen bonding motif a high enantioselectivity in the manganese-catalysed oxygenation of quinolone analogues (27 examples, 18–64% yield, 80–99% ee) was achieved. The site-selectivity was completely altered in favour of a less reactive but more accessible position. A Mn porphyrin complex with a remote hydrogen bonding motif induces a high enantioselectivity in the oxygenation of 3-alkylquinolones. Compared to an achiral Mn complex, the site-selectivity was completely altered in favour of less reactive methylene groups.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8252284ef81381eb4f3c5f5116ec5c6e http://europepmc.org/articles/PMC8150113 Zobrazit plný text záznamu