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2019•The Journal of Organic ChemistryRequires access

2-Substituted 1,4-Naphthoquinones in [6 + 4]-Cycloaddition with 8,8-Dicyanoheptafulvene

Marta Romaniszyn, Katarzyna Gronowska, Łukasz Albrecht

Open publisher page 24 citations

Abstract

This study demonstrates that classical lowest unoccupied molecular orbital reactivity of 2-substituted 1,4-naphthoquinones is possible to be reversed by deprotonation and application of the resulting dienolate as a 4π component in the higher-order [6 + 4]-cycloaddition proceeding in a completely pericyclic manner. 8,8-Dicyanoheptafulvene was shown to be an efficient 6π component in the developed reaction opening the access to functionalized cycloadducts in a diastereoselective manner by employing organocatalytic activation. Attempts to introduce enantioselective version of the developed higher-order cycloaddition were also undertaken.

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What this paper is about

This study demonstrates that classical lowest unoccupied molecular orbital reactivity of 2-substituted 1,4-naphthoquinones is possible to be reversed by deprotonation and application of the resulting dienolate as a 4π component in the higher-order [6 + 4]-cycloaddition proceeding in a completely pericyclic manner. 8,8-Dicyanoheptafulvene was shown to be an efficient 6π component in the developed reaction opening the access to functionalized cycloadducts in a diastereoselective manner by employing organocatalytic activation. Attempts to introduce enantioselective version of the developed higher-order cycloaddition were also undertaken.

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OpenAlex reports 24 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available abstract

This study demonstrates that classical lowest unoccupied molecular orbital reactivity of 2-substituted 1,4-naphthoquinones is possible to be reversed by deprotonation and application of the resulting dienolate as a 4π component in the higher-order [6 + 4]-cycloaddition proceeding in a completely pericyclic manner. 8,8-Dicyanoheptafulvene was shown to be an efficient 6π component in the developed reaction opening the access to functionalized cycloadducts in a diastereoselective manner by employing organocatalytic activation. Attempts to introduce enantioselective version of the developed higher-order cycloaddition were also undertaken.

Key concepts: Cycloaddition, Pericyclic reaction, Deprotonation, Chemistry, Reactivity (psychology), Enantioselective synthesis, Component (thermodynamics), Computational chemistry

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2-Substituted 1,4-Naphthoquinones in [6 + 4]-Cycloaddition with 8,8-Dicyanoheptafulvene — Research Paper | ScholarLens