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Organocatalytic Site-Selective Acylation of Carbohydrates and Polyol Compounds

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Site-Selective Catalysis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 372))

Abstract

Development and scope of conventionally difficult molecular transformation on site-selective acylation of carbohydrates and polyol compounds are described. A salient feature is that the site-selectivity can be controlled independently from the intrinsic reactivity of the substrate, i.e., catalyst-controlled selectivity. Therefore, some substrates undergo acylation with reversal of their intrinsic reactivity. The mechanistic aspects of catalyst-controlled site-selective acylation are discussed with the emphasis on the strategy relying on the accelerative reaction rather than the decelerative one. An unconventional retrosynthetic route based on catalyst-controlled site-selective acylation is proposed toward extremely short-step total synthesis of natural glycosides of an ellagitannin family. Application to the late-stage functionalization of the complex natural products of biological interest is also described.

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Authors and Affiliations

  1. Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-011, Japan

    Yoshihiro Ueda & Takeo Kawabata

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  1. Yoshihiro Ueda
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  2. Takeo Kawabata
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Correspondence to Takeo Kawabata .

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  1. Institute for Chemical Research Kyoto University, Kyoto, Japan

    Takeo Kawabata

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Ueda, Y., Kawabata, T. (2015). Organocatalytic Site-Selective Acylation of Carbohydrates and Polyol Compounds. In: Kawabata, T. (eds) Site-Selective Catalysis. Topics in Current Chemistry, vol 372. Springer, Cham. https://doi.org/10.1007/128_2015_662

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