Chiral Brønsted acid mediated glycosylation with recognition of alcohol chirality

Tomoya Kimura; Maiko Sekine; Daisuke Takahashi; Kazunobu Toshima

doi:10.1002/anie.201304830

Chiral Brønsted acid mediated glycosylation with recognition of alcohol chirality

Tomoya Kimura, Maiko Sekine, Daisuke Takahashi, Kazunobu Toshima

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

51 Citations (Scopus)

Abstract

Sugar sugar: In the glycosylation of racemic alcohols with 1 using the chiral phosphoric acid 2 as an activator, one enantiomer of the racemic alcohol selectively reacts with 1 to give the corresponding glycoside with good to excellent α/β-stereo- and diastereoselectivity in high yield. The reaction was successfully applied to the synthesis of a chiral natural flavan glycoside using a racemic aglycon.

Original language	English
Pages (from-to)	12131-12134
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	46
DOIs	https://doi.org/10.1002/anie.201304830
Publication status	Published - 2013 Nov 11

Keywords

diastereoselectivity
glycosides
glycosylation
organocatalysis
synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201304830

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AU - Sekine, Maiko

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

PY - 2013/11/11

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AB - Sugar sugar: In the glycosylation of racemic alcohols with 1 using the chiral phosphoric acid 2 as an activator, one enantiomer of the racemic alcohol selectively reacts with 1 to give the corresponding glycoside with good to excellent α/β-stereo- and diastereoselectivity in high yield. The reaction was successfully applied to the synthesis of a chiral natural flavan glycoside using a racemic aglycon.

KW - diastereoselectivity

KW - glycosides

KW - glycosylation

KW - organocatalysis

KW - synthetic methods

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Chiral Brønsted acid mediated glycosylation with recognition of alcohol chirality

Abstract

Keywords

ASJC Scopus subject areas

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