Extension of the Scope of Anionic Cycloadditions by Activating Organoelement Groups

Tandem C−C Bond-Forming Processes: Interception of the Pd-Catalyzed Decarboxylative Allylation of Allyl Diphenylglycinate Imines with Activated Olefins

“…Despite the relatively high basicity of the putative α-imino anion intermediate, the presence of water does not significantly impact the transformation (Table , entry 6). This stands in marked contrast to the 2-azaallyllithium dipolar nucleophiles described by Kauffmann and Pearson …”

Cycloadditions of Nonstabilized 2‐Azaallyllithiums (2‐Azaallyl Anions) and Azomethine Ylides with Alkenes: [3 + 2] Approaches to Pyrrolidines and Application to Alkaloid Total Synthesis.

“…Terminal alkynes, internal alkynes with propargylic hydrogens, and allenes are not useful because of their acidity. Vinyl sulfides, vinyl selenides, and vinyl silanes, alkenes that were also explored by Kauffmann with semistabilized 2-azaallyllithiums, 32 are excellent anionophiles that also lead to the installation of useful functional groups into the cycloadducts. Alkenes bearing no activating group (norbornene, 1-hexene, cyclohexene, ethyl vinyl ether) are too unreactive to intercept nonstabilized 2-azaallyllithiums prior to anion decomposition.…”