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Huiqing Deng

Bio: Huiqing Deng is an academic researcher from Anhui University of Technology. The author has contributed to research in topics: Lewis acids and bases & Trifluoromethanesulfonate. The author has co-authored 1 publications.

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TL;DR: In this paper, annulations of oxindole based spirocyclic donor-acceptor cyclopropanes and ynamides catalyzed by copper triflate have been developed for the synthesis of biologically important spirocyclopenteneoxindoles.
Abstract: [3 + 2] annulations of oxindole based spirocyclic donor–acceptor cyclopropanes and ynamides catalyzed by copper triflate have been developed for the synthesis of biologically important spirocyclopenteneoxindoles. These reactions tolerated a wide scope of substrates and provided the desired products in good to high yields (up to 90%) with up to >40 : 1 diastereoselectivities under mild conditions.

4 citations


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TL;DR: In this article , a multigram synthesis of 4-(dimethylamino)pyridinium azide, a stable, nonexplosive, low-hygroscopic source of azide ion soluble in both protic and aprotic organic solvents, was reported.
Abstract: We report a procedure for the multigram synthesis of 4-(dimethylamino)pyridinium azide, a stable, non-explosive, low-hygroscopic source of azide ion soluble in both protic and aprotic organic solvents. In protic ionic liquid media this reagent was shown to serve as a safer equivalent of toxic and unstable hydrazoic acid. The synthetic utility of this system was demonstrated using donor-acceptor cyclopropane ring opening as a model process. General procedures furnishing a variety of dialkyl (2-azido-2-arylethyl)malonates or 4-azido-4-arylbutyrates, depending on the protic ionic liquid applied, were elaborated. The conversion times for studied donor-acceptor cyclopropanes were established providing the relative reactivity sequence. The application of 4-(dimethylamino)pyridinium azide for a conventional nucleophilic substitution, oxirane ring opening, (3+2)-cycloaddition to (thio)cyano group as well as their combinations realized as telescopic synthesis was also demonstrated.

3 citations

Journal ArticleDOI
TL;DR: In this paper , an organocatalytic cascade approach for the synthesis of spiro-cyclopropyl oxindole derivatives has been developed based on asymmetric vinylogous Michael addition of 4-nitroisoxazole derivatives to N-Boc isatylidene malonates followed by intramolecular alkylation.
Abstract: A novel organocatalytic cascade approach for the synthesis of spiro-cyclopropyl oxindole derivatives has been developed. The methodology is based on asymmetric vinylogous Michael addition of 4-nitroisoxazole derivatives to N-Boc isatylidene malonates followed by intramolecular alkylation. Its remarkable stereocontrol, wide substrate scope, and scalability highlight this new developed strategy. Moreover, this work represents the first example of vinylogous Michael initiated ring closure (MIRC) reaction for the synthesis of chiral 3,3'-cyclopropyl oxindole.

1 citations

Journal ArticleDOI
TL;DR: A series of 1,6-diketone derivatives were prepared by first copper (II) trifluoromethanesulfonate catalysed ring-opening of cyclopropyl ketones with 1,3Diketones followed by DBU-promoted retro-Claisen-type reactions as mentioned in this paper .

1 citations

Journal ArticleDOI
TL;DR: Asymmetric ring-opening reactions of donor-acceptor cyclopropanes with 1,3-cyclodiones have been established for the synthesis of enantioenriched γ-hydroxybutyric acid derivatives in the presence of Cu(ii)/trisoxazoline catalyst as mentioned in this paper .
Abstract: Asymmetric ring-opening reactions of donor–acceptor cyclopropanes with 1,3-cyclodiones have been established for the synthesis of enantioenriched γ-hydroxybutyric acid derivatives in the presence of Cu(ii)/trisoxazoline catalyst. These reactions offered the desired products in 70% to 93% yields with 79% to 99% enantiomeric excesses.