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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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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… Click to show full 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.

Keywords: via borrowing; borrowing hydrogen; amino alcohols; reaction; alcohols via

Journal Title: Organic chemistry frontiers
Year Published: 2018

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