DABCO-catalyzed ring opening of activated cyclopropanes and recyclization leading to γ-lactams with an all-carbon quaternary center.

Domino ring-opening/recyclization reactions of doubly activated cyclopropanes as a strategy for the synthesis of furoquinoline derivatives.

A mild procedure for the Lewis acid-catalyzed ring-opening of activated cyclopropanes with amine nucleophiles.

The Lewis acid-catalyzed ring-opening of methyl 1-nitrocyclopropanecarboxylates with amine nucleophiles is described. The reaction proceeds at room temperature and with complete preservation of the enantiomeric purity from the electrophilic center of the cyclopropane to the acyclic product. The methodology was applied in an enantioselective synthesis of the dual serotonin/norepinephrine reuptak...

Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: synthesis of spirocyclic γ-lactams.

An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).

A unique Pd-catalysed Heck arylation as a remote trigger for cyclopropane selective ring-opening

Combining functionalization at a distant position from a reactive site with the creation of several consecutive stereogenic centres, including the formation of a quaternary carbon stereocentre, in acyclic system represents a pinnacle in organic synthesis. Here we report the regioselective Heck arylation of terminal olefins as a distant trigger for the ring-opening of cyclopropanes. This Pd-cata...

Disulfide catalyzed the highly regioselective conversion of epoxides to halohydrins with elemental halogens

The regioselective ring opening of styrene oxide using elemental iodine and bromine in the presence of disulfides as new catalysts was studied. The conductivity titration and UV spectroscopy were used to study the interaction of iodine with these catalysts. The results indicate that disulfide 11 is efficient in polyiodide formation, and can catalyze this reaction in excellent yield and high reg...