Domino Grignard Addition and Oxidation for the One-Pot Synthesis of C2-Quaternary 2‑Hydroxyindoxyls

We herein delineate an unexplored reactivity of 3-hydroxyoxindoles toward Grignard addition enabling a rapid access to a broad range of unnatural C2-quaternary 2-hydroxyindoxyls in high yields. The reaction proceeds via a mechanistically intriguing one-pot 1,2-hydride shift followed by autoxidation...

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Bibliographic Details
Published in:Organic letters 2019-10, Vol.21 (19), p.8044-8048
Main Authors: Mandal, Tirtha, Chakraborti, Gargi, Maiti, Subhadip, Dash, Jyotirmayee
Format: Article
Language:English
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Summary:We herein delineate an unexplored reactivity of 3-hydroxyoxindoles toward Grignard addition enabling a rapid access to a broad range of unnatural C2-quaternary 2-hydroxyindoxyls in high yields. The reaction proceeds via a mechanistically intriguing one-pot 1,2-hydride shift followed by autoxidation pathway. The utility of this method is demonstrated by the synthesis of a new class of bis-indoxyl spirofuran derivatives.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03022