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.

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Cheng, C., Wan, B., Zhou, B., Gu, Y., & Zhang, Y. (2019). Enantioselective synthesis of quaternary 3,4-dihydroisoquinolinones: Via Heck carbonylation reactions: Development and application to the synthesis of Minalrestat analogues. Chemical Science, 10(42), 9853–9858. https://doi.org/10.1039/c9sc03406d

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