A 1,1'-disubstituted ferrocenyl pyrroloimidazolone with syn stereochemistry undergoes double lithiation-electrophile quench in a one-pot procedure to give C 2 -symmetric 1,1',2,2'tetrasubstituted products in > 95 : 5 diastereomeric ratio (dr). These results represent an extension of double lithiation to access tetrasubstituted planar chiral ferrocenes for the first time to a nitrogen-linked (pyrroloimidazolone) chiral directing group.The stereochemistry of the products was determined by X-ray crystallography of distannane and dibromide adducts in combination with deuteration, elimination, and transmetalation experiments. Results support that products arise from selective deprotonation of the pro-S p position of each cyclopentadienyl (Cp) ring.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.