Stereoselective synthesis of pyrazolidinones via dipolar cycloaddition of azomethine imines with active esters under Lewis base catalysis is presented. The active esters are readily generated in situ from the corresponding acids. Products, which are obtained with excellent diastereocontrol and high enantioselectivity, contain along with the pyrazolidinone core also the tetrahydroisoquinoline st...

The Rh(II)-catalyzed formal [3+2] and [3+3] cycloadditions of 1-tosyl 1,2,3-triazoles with 2H-azirines have been developed, which enable the efficient synthesis of polysubstituted 3-aminopyrroles and 1,2-dihydropyrazines, respectively. The reported [3+2] cycloaddition represents the first application of 1-sulfonyl 1,2,3-triazole as a [2C]-component in relevant cycloaddition reactions.

The development of intermolecular [2 + 2]-cycloaddition of α-iodo-unsaturated ketones in the presence of diisobutylaluminum hydride (Dibal-H) is reported to produce various trispirocyclic derivatives containing a cyclobutane ring. This sequential lactonization/[2 + 2]-cycloaddition proceeds in high regioselectivity under mild conditions.

Metal-azide-metal-acetylide cycloaddition (iClick) reactions to synthesize heterotrimetallics and an unexpected novel tetranuclear gold(I) complex, are described. In addition, a discussion regarding the connection between traditional azide-alkyne cycloaddition reactions and iClick is presented focusing on applications towards linking multiple metal ions.

Intramolecular transannular dipolar cycloaddition was investigated as a key step in a synthetic approach to the core of the sarain alkaloids; although the use of an azomethine ylide was unsuccessful with the chosen aldehyde substrate, cycloaddition with a nitrone did give the alternative regioisomeric bridged cycloadduct.

7-Aryl-1,3,5-cycloheptatrienes react intermolecularly with methylenecyclopropanes in a triple gold(I)-catalyzed reaction to form cyclopentenes. The same formal (4+1) cycloaddition occurs with cyclobutenes. Other precursors of gold(I) carbenes can also be used as the C1 component of the cycloaddition.

Nickel(0) catalyzed [4+2] cycloaddition of electron-deficient dienes to alkynes and subsequent aromatization gave highly substituted arenes. This formal inverse electron-demand Diels-Alder cycloaddition is attributed to the formation of a seven-membered nickelacycle from a diene and an alkyne.

Total synthesis of ceratopicanol (1) was achieved with a tandem cycloaddition reaction of allenyl diazo compound 6 via a trimethylenemethane (TMM) diyl intermediate. The TMM diyl mediated [2+3] cycloaddition reaction furnished the consecutive quaternary carbon centers and showed an unusual diastereoselectivity.

In this protocol, we report a novel approach for the synthesis of a new class of heterocyclic 1H-1,2,3-triazole-modified peptidomimetic compounds. The process consists of an Ugi four-component condensation reaction of amines, an isocyanide, an aldehyde and acids followed by a Huisgen 1,3-dipolar cycloaddition reaction with an azide group in the presence of a catalytic amount of CuSO4</...

For the first time [3 + 2] 1,3-cycloaddition of an ionized carbonyl ylide has been observed in gas phase ion-molecule reactions of CH2OCH2 (1) with several carbonyl compounds. The reaction, which competes with electrophilic addition that leads to net CH2 transfer, occurs across the CdO double bond of acetaldehyde and several acyclic ketones yielding ionized 4,4-dialkyl-1,3-dioxolanes as unstabl...