Domino Ring Expansion: Regioselective Access to 9-Membered Lactones with a Fused Indole Unit from 2-Nitrophenyl-1,3-cyclohexanediones

Chemistry : a European Journal
David Reyes LoyaMichaël De Paolis

Abstract

The domino anionic fragmentation of 2-nitrophenyl-1,3-cyclohexanediones containing an electrophilic appendage such as aldehyde and epoxide is disclosed. This reaction, initiated by a series of nucleophiles, involves the generation of an intermediate hydroxylate followed by the regioselective formation and fragmentation of an intermediate lactolate into enolate. This strategy, devoid of any protecting group, enlarges the initial ring and provides an original access to decorated 9-membered lactones with a fused indole unit.

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Citations

Jul 17, 2018·Chemistry : a European Journal·Thomas C StephensWilliam P Unsworth
Aug 10, 2018·Chemistry : a European Journal·David Reyes Loya, Michaël De Paolis
Jan 26, 2021·Organic & Biomolecular Chemistry·Kleopas Y PalateWilliam P Unsworth
Mar 2, 2020·Chemical Science·Aimee K Clarke, William P Unsworth
Jul 3, 2021·Angewandte Chemie·Guillaume ForceDavid Lebœuf

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