Aza--Quinone Methide Promoted Strain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into Functionalized Azetidines.

A strategy for activating azabicyclo[1.1.0]butane (ABB) with generated aza--quinone methide, promoted by HFIP, is reported.

Hydrogen bonding-promoted tunable approach for access to aza-bicyclo-[3.3.0]octanes and cyclopenta[] pyrroles.

A unified strategy is disclosed that builds on successfully engaging the aniline nitrogen of 1,3-amphoteric γ-aminocyclopentenone for a tandem annulation with electron-poor alkynes, solely assisted by the H-bonding network of HFIP. This metal-free mild strategy provides access to medicinally relevant aza-bicyclo-octanes en route to another important scaffold: cyclopenta[]pyrrole.

Fe-Catalyzed Hydroallylation of Unactivated Alkenes with Vinyl Cyclopropanes.

Catalytic, reductive C-C bond formation between alkenes and vinyl cyclopropane (VCP) through hydrogen atom transfer (MHAT) is developed. Despite VCP's use as probes in radical-clock experiments, translation of this manifold into synthetic methods for accessing elusive C-C bonds remains largely unexplored. This work represents the first foray into this front where the high chemoselectivity of MHAT for alkene over VCP was pivotal for realizing the strategy.