Cu-Catalyzed Chemodivergent, Stereoselective Propargylic Dearomatization and Etherification of 2-Naphthols

Das, Braja Gopal; Shah, Sadhna; Das, Arko; Singh, Vinod K.

doi:10.1021/acs.orglett.1c02027

Cited by 14 publications

(8 citation statements)

References 55 publications

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“…近年来被广泛研究的不对称去芳构化反应(CADA) 是形成新的碳-碳键的有效手段. β-萘酚去芳构化可构建许多活性分子中的萘酮骨架 [39][40][41] , 探索具有高位点选择性和立体选择性的 β-萘酚 α 位的去芳构化反应具有重要意义.…”

Section: 其它类型的烷基化反应unclassified

Recent Advances in the Reactions of β-Naphthol at α-Position

Liu¹,

Chen²,

Liu³

et al. 2023

Chinese Journal of Organic Chemistry

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β-Naphthol is an important synthon in organic synthesis and can participate in various chemical reactions due to its active chemical property at α-site, which has attracted a great attention from chemists. β-Naphthol can undergo various chemical transformations at α-position, such as alkylation, arylation, cyclization, amination, halogenation and so on, which can be used to construct structurally diverse naphthol derivatives with various biological activities. These naphthol derivatives can be used not only as the privileged skeletons of natural active drugs, but also as the building blocks for the preparation of the important intermediates in chemical synthesis. In recent years, chemical reactions based on β-naphthol at α-site have emerged one after another. The reactions of β-naphthol at α-position are reviewed from the aspects of C-

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Section: 其它类型的烷基化反应unclassified

Recent Advances in the Reactions of β-Naphthol at α-Position

Liu¹,

Chen²,

Liu³

et al. 2023

Chinese Journal of Organic Chemistry

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“…As electron-rich aromatic arenes, β-naphthols exhibit reactivity at the α-position with different electrophiles, facilitating the construction of diverse C–C, C–N, and C–X bonds . They can also undergo reactions with carbon electrophiles at oxygen, representing the primary side process in dearomatization reactions . The intramolecular CADA of β-naphthols, designed with an electrophilic partner adjacent to the hydroxyl group of β-naphthols, favored dearomatization over undesired O -functionalization [Figure b(1)] .…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Copper-Catalyzed Dearomative Spiroannulation of β-Naphthols or Indoles with Yne-Allylic Esters

Zhao,

Deng,

Huang

et al. 2024

ACS Catal.

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Catalytic asymmetric dearomatization reactions of α-unsubstituted β-naphthols are very challenging due to the high energy barrier resulting from the loss of aromaticity. Herein, we describe an example of enantioselective catalytic dearomative spiroannulation with yne-allylic esters. The success of this reaction relied on the copper-catalyzed remote asymmetric strategy using yne-allylic esters as the bis-electrophilic reagents. This transformation features mild reaction conditions, broad functional group tolerance, and an extensive substrate scope, thereby facilitating the efficient construction of an array of enantioenriched naphthalene-2-one and spiroindolenine derivatives. Experimental studies and density functional theory calculations establish the reaction pathway and origin of stereoselectivity.

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“…1, F). 12 With its wide applications, beta-naphthol has been functionalized via different transformations: alkylation, [13][14][15][16][17][18][19][20][21][22] cyclization, 16,[23][24][25][26][27][28][29] and arylation. [30][31][32][33][34][35] In particular, C-H functionalization of arenols via Friedel-Crafts (FC) alkylation reaction constructs a new C-C bond.…”

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confidence: 99%