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Issue 42, 2016
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Diastereoselective sp2–sp3 coupling of sugar enol ethers with unactivated cycloalkenes: new entries to C-branched sugars

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Abstract

Sugar enol ethers undergo efficient coupling at C-2 with unactivated cycloalkenes under a low Pd loading affording allylic substitution products. High diastereoselectivity was observed at the allylic centre with sterically hindered substrates. Generation of a π-allyl complex by the Pd(II) catalyst via cleavage of the allylic C–H bond of the cycloalkene may be responsible for the formation of sp2–sp3 coupling products.

Graphical abstract: Diastereoselective sp2–sp3 coupling of sugar enol ethers with unactivated cycloalkenes: new entries to C-branched sugars

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Publication details

The article was received on 04 Sep 2016, accepted on 04 Oct 2016 and first published on 04 Oct 2016


Article type: Communication
DOI: 10.1039/C6OB01949H
Citation: Org. Biomol. Chem., 2016,14, 9989-9992
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    Diastereoselective sp2–sp3 coupling of sugar enol ethers with unactivated cycloalkenes: new entries to C-branched sugars

    N. Hussain, M. B. Tatina, F. Rasool and D. Mukherjee, Org. Biomol. Chem., 2016, 14, 9989
    DOI: 10.1039/C6OB01949H

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