No abstract

The synthesis of fully substituted carbon stereocenters remains a challenging task in organic chemistry. Recent developments in the design of substrates that undergo the Nazarov cyclization have enabled this reaction to become a valuable way to form elaborately substituted cyclopentane rings containing fully substituted carbon stereocenters. Three major strategies have been utilized in this endeavor. Here we provide an overview of these three areas that should give insight into the usage of the Nazarov reaction for the challenging task of forming fully substituted carbon stereocenters.

The aza-Piancatelli rearrangement with hydroxylamines to 4-aminocyclopentenones is described. Subsequent transformations highlight the versatility of the cyclopentene scaffold and the value of the hydroxylamine in this transformation.

The development of a new platform to initiate the cascade rearrangement of furans for the formation of functionalized cyclopentenone building blocks is reported. This methodology allows the creation of congested vicinal stereogenic centers with high diastereoselectivity through a 4π-electrocyclization process.