Organopromoted Selectivity-Switchable Synthesis of Polyketones

In this work, an organopromoted metal-free pharmaceutical-oriented selectivity-switchable benzylic oxidation was developed, affording mono-, di-, and trioxygenation products, respectively, using oxygen as the oxidant under mild conditions. This process facilitates dioxygenation of 2,6-benzylic posit...

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Bibliographic Details
Published in:Organic letters 2017-10, Vol.19 (20), p.5593-5596
Main Authors: Liu, Jie, Hu, Kang-Fei, Qu, Jian-Ping, Kang, Yan-Biao
Format: Article
Language:English
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Summary:In this work, an organopromoted metal-free pharmaceutical-oriented selectivity-switchable benzylic oxidation was developed, affording mono-, di-, and trioxygenation products, respectively, using oxygen as the oxidant under mild conditions. This process facilitates dioxygenation of 2,6-benzylic positions of heterocycles, which could be inhibited by heterocycle chelation to the metal cocatalysts. Enantiopure chiral ketones could also be prepared. The noninvolvement of transition metals and toxins avoids metal or hazardous residues, consequently ensuring a final-stage gram-scale synthesis of Lenperone.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02731