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Enantioselective synthesis of quaternary 3,4-dihydroisoquinolinones via Heck carbonylation reactions: development and application to the synthesis of Minalrestat analogues

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Abstract

Minalrestat and its analogues represent structurally novel aldose reductase inhibitors, and the asymmetric synthesis of such pharmaceutically privileged molecules has not been reported yet. We have developed a palladium-catalyzed enantioselective intramolecular carbonylative Heck reaction by using formate esters as the source of CO, which represents the first enantioselective synthesis of quaternary 3,4-dihydroisoquinolines. The reaction provides a facile and efficient method for the synthesis of enantiopure nitrogen-containing heterocyclic compounds bearing an all-carbon quaternary stereocenter. The reaction has been successfully applied to the first asymmetric synthesis of Minalrestat analogues.

Graphical abstract: Enantioselective synthesis of quaternary 3,4-dihydroisoquinolinones via Heck carbonylation reactions: development and application to the synthesis of Minalrestat analogues

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Publication details

The article was received on 10 Jul 2019, accepted on 31 Aug 2019 and first published on 03 Sep 2019


Article type: Edge Article
DOI: 10.1039/C9SC03406D
Chem. Sci., 2019, Advance Article
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    Enantioselective synthesis of quaternary 3,4-dihydroisoquinolinones via Heck carbonylation reactions: development and application to the synthesis of Minalrestat analogues

    C. Cheng, B. Wan, B. Zhou, Y. Gu and Y. Zhang, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03406D

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