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Squaramide-catalyzed enantioselective Michael addition of nitromethane to 2-enoylazaarenes: synthesis of chiral azaarene-containing γ-nitroketones.

ABSTRACT: Bifunctional chiral squaramide-catalyzed highly enantioselective Michael addition of nitromethane to diverse 2-enoylazaarenes was successfully performed. This protocol provided a set of chiral azaarene-containing γ-nitroketones with up to 98% yield and 98% ee in a solvent-free catalytic system under mild conditions. Furthermore, gram-scale synthetic utility was also showcased.

SUBMITTER: Huang HP

PROVIDER: S-EPMC11192089 | biostudies-literature | 2024 Jun

REPOSITORIES: biostudies-literature

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Squaramide-catalyzed enantioselective Michael addition of nitromethane to 2-enoylazaarenes: synthesis of chiral azaarene-containing γ-nitroketones.

Huang Hong-Ping HP Xie Yu-Hang YH Gan Xu-Mei XM Wen Xin-Yu XY Wang Cui-Xia CX Deng Yan-Qiu YQ Zhang Zhen-Wei ZW

RSC advances 20240621 28

Bifunctional chiral squaramide-catalyzed highly enantioselective Michael addition of nitromethane to diverse 2-enoylazaarenes was successfully performed. This protocol provided a set of chiral azaarene-containing γ-nitroketones with up to 98% yield and 98% ee in a solvent-free catalytic system under mild conditions. Furthermore, gram-scale synthetic utility was also showcased. ...[more]

PMID: 38911828

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