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Issue 10, 2018
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Divergent reactions of oxindoles with amino alcohols via the borrowing hydrogen process: oxindole ring opening vs. C3 alkylation

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Abstract

Oxindoles display a diverse pattern of reactivity upon reaction with different classes of amino alcohols via the borrowing hydrogen process. Whereas the reaction with N-acetyl amino alcohols leads to C3 alkylation, the reaction with N-alkyl amino alcohols results in the formation of synthetically useful α-aryl-lactams via a remarkably facile oxindole ring-opening reaction. Reactions occurred with quantitative conversion and selectivity under relatively mild reaction conditions.

Graphical abstract: Divergent reactions of oxindoles with amino alcohols via the borrowing hydrogen process: oxindole ring opening vs. C3 alkylation

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Publication details

The article was received on 19 Feb 2018, accepted on 20 Mar 2018 and first published on 21 Mar 2018


Article type: Research Article
DOI: 10.1039/C8QO00184G
Citation: Org. Chem. Front., 2018,5, 1622-1627
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    Divergent reactions of oxindoles with amino alcohols via the borrowing hydrogen process: oxindole ring opening vs. C3 alkylation

    G. Di Gregorio, M. Mari, S. Bartolucci, F. Bartoccini and G. Piersanti, Org. Chem. Front., 2018, 5, 1622
    DOI: 10.1039/C8QO00184G

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