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Title: Iridium-promoted deoxyglycoside synthesis : stereoselectivity and mechanistic insight
Authors: Pal, Kumar Bhaskar
Guo, Aoxin
Das, Mrinmoy
Lee, Jiande
Báti, Gábor
Yip, Benjamin Rui Peng
Loh, Teck-Peng
Liu, Xue-Wei
Keywords: Science::Chemistry
Issue Date: 2021
Source: Pal, K. B., Guo, A., Das, M., Lee, J., Báti, G., Yip, B. R. P., Loh, T. & Liu, X. (2021). Iridium-promoted deoxyglycoside synthesis : stereoselectivity and mechanistic insight. Chemical Science, 12(6), 2209-2216.
Project: NRF2016NRF-NSFC002-005
Journal: Chemical Science
Abstract: Herein, we devised a method for stereoselective O-glycosylation using an Ir(I)-catalyst which enables both hydroalkoxylation and nucleophilic substitution of glycals with varying substituents at the C3 position. In this transformation, 2-deoxy-α-O-glycosides were acquired when glycals equipped with a notoriously poor leaving group at C3 were used; in contrast 2,3-unsaturated-α-O-glycosides were produced from glycals that bear a good leaving group at C3. Mechanistic studies indicate that both reactions proceed via the directing mechanism, through which the acceptor coordinates to the Ir(I) metal in the α-face-coordinated Ir(I)-glycal π-complex and then attacks the glycal that contains the O-glycosidic bond in a syn-addition manner. This protocol exhibits good functional group tolerance and is exemplified with the preparation of a library of oligosaccharides in moderate to high yields and with excellent stereoselectivities.
ISSN: 2041-6520
DOI: 10.1039/D0SC06529C
Rights: © 2021 The Author(s). Published by the Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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