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

ABSTRACT: 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.

SUBMITTER: Burg F

PROVIDER: S-EPMC8150113 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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

Burg Finn F Breitenlechner Stefan S Jandl Christian C Bach Thorsten T

Chemical science 20200114 8

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. <i>Via</i> 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 s ...[more]

PMID: 34123300

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