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

Chemical Science
Finn BurgThorsten Bach

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.

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Citations

May 21, 2020·Organic & Biomolecular Chemistry·Yoichiro Kuninobu, Takeru Torigoe
Nov 28, 2020·Mikrochimica Acta·Xiaohui NiuKunjie Wang
May 20, 2021·Chemical Society Reviews·Giorgio OlivoStefano Di Stefano
Jan 14, 2021·Angewandte Chemie·Rajasekar Reddy AnnapureddyThorsten Bach
Jan 22, 2021·Nature Communications·Chi ZhangXin-Yuan Liu
Apr 27, 2021·Organic & Biomolecular Chemistry·Andreas KrauseBernd Schmidt
Sep 3, 2021·Chemistry, an Asian Journal·Jincheng XuHao Guo
Oct 6, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Miquel Costas

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Methods Mentioned

BETA
X-ray

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