The first chiral phosphoric acid catalyzed highly diastereo- and enantioselective 1,3-dipolar cycloaddition reaction of azlactones and methyleneindolinones was disclosed. By using a BINOL-derived chiral phosphoric acid as the catalyst, azlactones were activated as chiral anti N-protonated 1,3-dipoles to react with methyleneindolinones to yield biologically important 3,3'-pyrrolidonyl spirooxind...

The Pd-catalyzed intramolecular alpha-arylation of amides is applied to the synthesis of functionalized spirooxindoles. The substrate scope is evaluated, and the reaction is demonstrated to be useful for the assembly of spirooxindole natural products and derivatives thereof. As an application, a new synthesis of horsfiline 1 is presented, giving the natural product in only 4 steps from commerci...

A highly enantioselective organocatalytic vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles to isatins has been achieved by using bifunctional organocatalysts. The unexpected intramolecular lactonization which follows the initial aldol reaction, leading to the cleavage of the oxindole ring and generation of enantioenriched spirooxindole dihydropyranones in good to excellen...

Chiral pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds. Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems. Derivatives of spirooxindole find very wide biological applications as anti micr...

Chiral pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds. Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems. Derivatives of spirooxindole find very wide biological applications as anti micr...

Novel spirooxindole-pyrazolines and spirobenzofuranone-pyrazolines have been synthesized in good to excellent yields via the annulation reactions of the corresponding 3-alkylideneoxindoles and 3-alkylidenebenzofuranones with Huisgen zwitterions. The preliminary bioassay demonstrated that some of the spiropyrazolines possess good in vitro fungicidal activity against several crop fungi at a conce...

The enantioselective preparation of pharmacologically interesting chroman-fused spirooxindole derivatives is described based on an organocatalytic multicomponent cascade reaction. The compounds synthesized using this method potently inhibited the proliferation of various cancer cell lines. The most potent compound (7e) induced caspase-independent apoptosis and cell cycle arrest in MCF-7 breast ...

A thermal [2 + 2] cycloaddition reaction of allene-ynes has been used to transform chiral non-racemic allenyl oxindoles into chiral non-racemic spirooxindoles containing an alkylidene cyclobutene moiety. The enantiomeric excesses were determined by chiral lanthanide shift NMR analysis and the transfer of chiral information from the allene to the spirooxindole was found to be greater than 95%.

A novel and convenient organocatalytic tandem reaction has been developed for the asymmetric assembly of saturated aldehydes (or enals), nitroolefins and isatins to produce six-membered oxa-spirooxindole backbones bearing four contiguous stereogenic centers and multiple functional groups with high stereoselectivity.

A mild and practical synthesis of spirooxindole [1,3]oxazino derivatives from N-substituted isatins and 1,3-dicarbonyl compounds with pyridine derivatives is reported. The reactions provided good to excellent yields. Further exploration of the molecular diversity of these compounds is demonstrated through Diels-Alder reactions.