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

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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https://hal-normandie-univ.archives-ouvertes.fr/hal-01793134
Contributor : Jérôme Blanchet <>
Submitted on : Wednesday, May 16, 2018 - 11:23:24 AM
Last modification on : Wednesday, July 1, 2020 - 12:44:30 PM

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David Reyes Loya, Alexandre Jean, Morgan Cormier, Catherine Fressigné, Stefano Nejrotti, et al.. Domino Ring Expansion: Regioselective Access to 9-Membered Lactones with a Fused Indole Unit from 2-Nitrophenyl-1,3-cyclohexanediones. Chemistry - A European Journal, Wiley-VCH Verlag, 2018, 24 (9), pp.2080-2084. ⟨10.1002/chem.201705645⟩. ⟨hal-01793134⟩

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