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

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 per...

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Published inJournal of organic chemistry Vol. 84; no. 16; pp. 9929 - 9936
Main Authors Romaniszyn, Marta, Gronowska, Katarzyna, Albrecht, Łukasz
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.08.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
TROPONE
CATALYSIS
CYCLOADDITION REACTIONS
CASCADE REACTIONS
ASYMMETRIC CYCLOADDITION
ALPHA-ARYLATION
8+2 ANNULATION
DERIVATIVES
CYCLIZATION
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01091