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Sodium Phenoxide−Phosphine Oxides as Extremely Active Lewis Base Catalysts for the Mukaiyama Aldol Reaction with Ketones

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2007, 9, 22, 4527-4530
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    Sodium Phenoxide−Phosphine Oxides as Extremely Active Lewis Base Catalysts for the Mukaiyama Aldol Reaction with Ketones
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    Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8603, Japan
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    Organic Letters

    Cite this: Org. Lett. 2007, 9, 22, 4527–4530
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    https://doi.org/10.1021/ol702052r
    Published September 26, 2007
    Copyright © 2007 American Chemical Society
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    Abstract

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    A highly efficient Mukaiyama aldol reaction between ketones and trimethylsilyl enolates catalyzed by sodium phenoxide−phosphine oxides as simple homogeneous Lewis base catalysts (0.5−10 mol %) was developed, which minimized competing retro-aldol reaction. For a variety of aromatic ketones and aldimines, aldol and Mannich-type products with an α-quaternary carbon center were obtained in good to excellent yields. Up to 100 mmol scale of benzophenone and trimethylsilyl enolate with 0.5 mol % of catalyst was established in 97% yield (34.8 g).

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    Organic Letters

    Cite this: Org. Lett. 2007, 9, 22, 4527–4530
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol702052r
    Published September 26, 2007
    Copyright © 2007 American Chemical Society
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