Domino Ring Expansion: Regioselective Access to 9-Membered Lactones with a Fused Indole Unit from 2-Nitrophenyl-1,3-cyclohexanediones - Normandie Université Access content directly
Journal Articles Chemistry - A European Journal Year : 2018

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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hal-01793134 , version 1 (16-05-2018)

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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, 2018, 24 (9), pp.2080-2084. ⟨10.1002/chem.201705645⟩. ⟨hal-01793134⟩
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