In this work, we present a new strategy for the chemo-, regio-, and stereoselective synthesis of functionalized pyrrolidine derivatives via a hydroxy-assisted phosphine-catalyzed reaction of allenoates or substituted allenoates with o-hydroxyaryl azomethine ylides that offers a wide variety of 4-methylenepyrrolidine derivatives in synthetically useful yields with high stereoselctivities under mild conditions. Remarkably, it is the first example of highly regio- and stereoselective phosphine-catalyzed [3 + 2] cycloaddition of allenoates with o-hydroxyaryl azomethine ylides.

A triethylamine-catalyzed domino reaction between phthalimidomalonate derivatives and activated alkynes has been developed. This catalytic protocol is applicable to the synthesis of structurally functionalized N-fused tricyclic 3-hydroxyisoindolin-1-ones.

A phosphine-mediated domino reaction between phthalimidomalonates and allenoates furnishes highly functionalized pyrroloisoindolinone derivatives in synthetically useful yields. When ethyl but-2-ynoate was reacted with phthalimidomalonates under the same conditions, pyrroloisoindolinone derivatives were also obtained in good to excellent yields. The mechanism for the transformation is a tandem γ-umpolung/Wittig/γ-umpolung process. The present domino reaction not only exploits the potential of allenoates, but also extends the existing phosphine-mediated cyclization scope.

An efficient method for the synthesis of C-1 position acyl substituted pyrazoloquinazoline derivatives via a PBu3-promoted regioselective domino process of sulfonylhydrazones and alkynyl ketones was developed, which may be potentially useful for drug discovery.

An efficient method for the synthesis of structurally diverse functionalized tetrahydropyridazines via self [4 + 2] cycloaddition of in situ generated 1,2-diaza-1,3-dienes was developed, which may play an important role in drug discovery.

A novel method for the synthesis of diversely functionalized pyrazolo[5,1-a]isoindol-8(3aH)-ones is developed via phosphine-catalyzed tandem Michael addition/intramolecular Morita–Baylis–Hillman reaction of electron-deficient alkynes and N-amino substituted phthalimide. This cyclization is operationally simple under metal-free reaction conditions.

Highly stereoselective intermolecular reactions of electron-deficient alkynes with N-hydroxyphthalimides for efficient construction of N-unprotected 3-methyleneisoindolin-1-ones have been developed through base catalytic strategies. The reaction of alkynoates with N-hydroxyphthalimides catalyzed by Bu3P in DMF at 150 °C gave the corresponding 3-methyleneisoindolin-1-ones with a (Z)-configuration, while the reaction of alkynoates with N-hydroxyphthalimides catalyzed by K2CO3 in DMF at 60 °C gave the corresponding 3-methyleneisoindolin-1-ones with an (E)-configuration, and (Z)-3-methyleneisoindolin-1-ones were obtained when alkyne ketones reacted with N-hydroxyphthalimide.

A group of 3-amino-2-pyrones were synthesized and their biological activities were evaluated for inhibiting cyclooxygenase (COX) activity. This study has led to the identification of COX-1-selective inhibitors. Among the tested compounds, the compound 5j exhibited the most potent COX-1 inhibitory activity (IC50 = 19.32 μg/mL) and COX-1 selectivity index (SI = 41.98).A group of 3-amino-2-pyrones were synthesized and their biological activities were evaluated for inhibiting cyclooxygenase (COX) activity. This study has led to the identification of COX-1-selective inhibitors. Among the tested compounds, the compound 5j exhibited the most potent COX-1 inhibitory activity (IC50 = 19.32 mg/mL) and COX-1 selectivity index (SI;1; = 41.98).

Spirocyclopenteneoxindole derivatives were obtained by stereoselective triphenylphosphine-catalyzed [3+2] cycloadditions of ynones and alkylidene oxindole derivatives. This approach is based on the Michael addition of ynones to alkylidene oxindole derivatives, followed by intermolecular \(\upalpha \)-addition using 50 mol% triphenylphosphine as catalyst.

A stereoselective and effective method for the synthesis of vinyl thioethers has been developed. This method is based on the Michael addition of ethanethiol to various alkynyl ketones using 10 mol% of tributylphosphine as catalyst. Most of alkynyl ketones react with ethanethiol in this system to yield mainly Z-isomer of vinyl thioether adducts, only in one case mainly E-isomer of vinyl thioether adducts was observed.

A triethylamine-catalyzed domino reaction between phthalimidomalonate derivatives and activated alkynes has been developed. This catalytic protocol is applicable to the synthesis of structurally functionalized N-fused tricyclic 3-hydroxyisoindolin-1-ones.

A phosphine-mediated domino reaction between phthalimidomalonates and allenoates furnishes highly functionalized pyrroloisoindolinone derivatives in synthetically useful yields. When ethyl but-2-ynoate was reacted with phthalimidomalonates under the same conditions, pyrroloisoindolinone derivatives were also obtained in good to excellent yields. The mechanism for the transformation is a tandem γ-umpolung/Wittig/γ-umpolung process. The present domino reaction not only exploits the potential of allenoates, but also extends the existing phosphine-mediated cyclization scope.