Journal Article10.1002/9783527832217.ch16
Dearomative Organocatalytic Strategies
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TL;DR: In this article , an overview for the development of asymmetric dearomatizations of various heteroarenes and arenes via organocatalysis over the past decades is presented.
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Abstract: The asymmetric dearomative reactions can provide the complicated three-dimensional skeletons from easily available aromatic compounds. This chapter offers an overview for the development of asymmetric dearomatizations of various heteroarenes and arenes via organocatalysis over the past decades.
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Citations
Not antiaromaticity gain, but increased asynchronicity enhances the Diels-Alder reactivity of tropone.
TL;DR: In this paper , it was shown that the activation barrier is lower by increased asynchronicity, and that the higher reactivity of hydrazone ion analogs was attributed to a raised HOMO energy induced by antiaromaticity.
Aminocatalytic 1,6-Addition of 2-Benzyl-3-furaldehyde to 3-Cyano-4-styrylcoumarins: A Dearomative Approach for the Synthesis of Furan–Coumarin Hybrids
Aleksandra Topolska,Artur Przydacz,Lesław Sieroń,Anna Skrzynska,Alberto Fraile,José Alemán,Łukasz Albrecht +6 more
TL;DR: Aminocatalytic 1,6-addition of 2-benzyl-3-furaldehyde to 3-cyano-4-styrylcoumarins is achieved through temporary dearomatization, utilizing a catalytic system of aminocatalyst and acidic cocatalyst, yielding furan-coumarin hybrids with a wide substrate scope.
References
Organocatalytic asymmetric chlorinative dearomatization of naphthols
TL;DR: A highly enantioselective chlorinative dearomatization of 1-naphthol and 2- naphthols was realized for the first time, providing chiral naphthalenones with a Cl-containing all-substituted stereocenter in excellent yields and enantiOSElectivity.
Asymmetric Synthesis of Hydrobenzofuranones via Desymmetrization of Cyclohexadienones Using the Intramolecular Stetter Reaction
Qin Liu,Tomislav Rovis +1 more
TL;DR: Dearomatization of phenols followed by oxidation affords cyclohexadienyloxyacetaldehydes, which produce hydrobenzofuranones via asymmetric intramolecular Stetter reaction in good to excellent yield.
Enantioselective Total Synthesis of (−)‐Minovincine in Nine Chemical Steps: An Approach to Ketone Activation in Cascade Catalysis
TL;DR: The first enantioselective total synthesis of (-)-minovincine has been accomplished in nine chemical steps and 13 % overall yield thanks to a novel, one-step Diels-Alder/β-elimination/conjugate addition organocascade sequence.
Multiple Hydrogen-Bonding Bifunctional Thiourea-Catalyzed Asymmetric Dearomative [4 + 2] Annulation of 3-Nitroindoles: Highly Enantioselective Access to Hydrocarbazole Skeletons
Deng-Feng Yue,Jian-Qiang Zhao,Xiao-Zhen Chen,Yan Zhou,Xiao-Mei Zhang,Xiao-Ying Xu,Wei-Cheng Yuan +6 more
TL;DR: A method for the enantioselective construction of hydrocarbazole skeletons through dearomative [4 + 2] annulation of 3-nitroindoles with Nazarov reagents is reported.