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Regioselective Direct Difunctionalization of Glycals: Convenient Access to 2‐Deoxyglycoconjugates Mediated by Tetra‐n‐butylammonium Iodide/Sodium Periodate

Regioselective Direct Difunctionalization of Glycals: Convenient Access to 2‐Deoxyglycoconjugates... A combination of nBu4NI and NaIO4 promoted the intermolecular stereo and regioselective bisfunctionalization of glycals in a metal‐free, one‐pot process. The oxidative iodocaboxylation, iodoamination, and iodoazidation of enol ether moieties by employing carboxylic or aromatic acids, and N‐nucleophiles such as 1‐H‐benzotriazole or NaN3 led to glycosyl carboxylates, glycosyl amines, and glycosyl azides, respectively. The protocol is operationally simple, employs readily available and environmental benign reagents, and was applicable for a diverse range of substrates to obtain stereodivergent glycoconjugates in yields up to 99 % with diastereomeric ratios up to 100 %. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Regioselective Direct Difunctionalization of Glycals: Convenient Access to 2‐Deoxyglycoconjugates Mediated by Tetra‐n‐butylammonium Iodide/Sodium Periodate

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References (70)

Publisher
Wiley
Copyright
© 2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201500470
Publisher site
See Article on Publisher Site

Abstract

A combination of nBu4NI and NaIO4 promoted the intermolecular stereo and regioselective bisfunctionalization of glycals in a metal‐free, one‐pot process. The oxidative iodocaboxylation, iodoamination, and iodoazidation of enol ether moieties by employing carboxylic or aromatic acids, and N‐nucleophiles such as 1‐H‐benzotriazole or NaN3 led to glycosyl carboxylates, glycosyl amines, and glycosyl azides, respectively. The protocol is operationally simple, employs readily available and environmental benign reagents, and was applicable for a diverse range of substrates to obtain stereodivergent glycoconjugates in yields up to 99 % with diastereomeric ratios up to 100 %.

Journal

Asian Journal of Organic ChemistryWiley

Published: Feb 1, 2016

Keywords: ; ; ; ;

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