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Issue 16, 2018
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Secondary amine salt catalyzed controlled activation of 2-deoxy sugar lactols towards alpha-selective dehydrative glycosylation

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Abstract

A new organocatalytic glycosylation method exploiting the lactol functionality has been disclosed. The catalytic generation of glycosyl oxacarbenium ions from lactols under forcible conditions via weakly Brønsted-acidic, readily available secondary amine salts affects the diastereoselective glycosylation of 2-deoxypyranoses and furanoses. This operationally simple iminium catalyzed activation of 2-deoxy hemi-acetals is a potential alternative to the existing cumbersome methods that need specialized handling. The mechanisms for this unique transformation and kinetic/thermodynamic effects have been discussed based on both experimental evidence and theoretical studies.

Graphical abstract: Secondary amine salt catalyzed controlled activation of 2-deoxy sugar lactols towards alpha-selective dehydrative glycosylation

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Publication details

The article was received on 17 Feb 2018, accepted on 29 Mar 2018 and first published on 29 Mar 2018


Article type: Communication
DOI: 10.1039/C8OB00423D
Citation: Org. Biomol. Chem., 2018,16, 2870-2875
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    Secondary amine salt catalyzed controlled activation of 2-deoxy sugar lactols towards alpha-selective dehydrative glycosylation

    T. Ghosh, A. Mukherji, H. K. Srivastava and P. K. Kancharla, Org. Biomol. Chem., 2018, 16, 2870
    DOI: 10.1039/C8OB00423D

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