Stereodefined Synthesis of Acyclic <i>meso</i> -2,3-Diaryl Dialdehydes and Their Iridium-Catalyzed Enantioselective Desymmetrization

Efficient enantioselective desymmetrization of acyclic meso -dialdehydes has remained unexplored due to limited substrate access. We report a stereodefined synthesis of acyclic meso -2,3-diaryl dialdehydes and their iridium-catalyzed enantioselective desymmetrization to give γ-butyrolactones in up to 96% ee. Hydrogen-donor-free conditions enable in situ Ir–hydride generation for certain substrates. This method enables catalytic asymmetric access to cinncassin A 1 .

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-06-26
DOI
https://doi.org/10.1021/acs.joc.6c00927
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
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article

Stereodefined Synthesis of Acyclic meso -2,3-Diaryl Dialdehydes and Their Iridium-Catalyzed Enantioselective Desymmetrization

Takayoshi Suzuki, Da‐Yang Zhou, Takeyuki Suzuki, Kaori Asano et al.
The Journal of Organic Chemistry
Asymmetric Hydrogenation and Catalysis
article

Stereodefined Synthesis of Acyclic meso -2,3-Diaryl Dialdehydes and Their Iridium-Catalyzed Enantioselective Desymmetrization

Takayoshi Suzuki, Da‐Yang Zhou, Takeyuki Suzuki, Kaori Asano, Runze Zhao
article en

Abstract

Efficient enantioselective desymmetrization of acyclic meso -dialdehydes has remained unexplored due to limited substrate access. We report a stereodefined synthesis of acyclic meso -2,3-diaryl dialdehydes and their iridium-catalyzed enantioselective desymmetrization to give γ-butyrolactones in up to 96% ee. Hydrogen-donor-free conditions enable in situ Ir–hydride generation for certain substrates. This method enables catalytic asymmetric access to cinncassin A 1 .

The Journal of Organic Chemistry
Midorigaoka Hospital (JP)
Openalex Percentile: Top 15%
Asymmetric Hydrogenation and Catalysis
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