Cyclic reaction with organocuprates

Treatment of cyclic vinylaziridine 105 with organocuprates of the R2CuLi type proceeds in a highly syn-selective manner (Scheme 2.29) [46], The syn stereochemistry of the reaction reflects the effect of the acetonide group, which directs the nucleophilic attack to the less hindered a-face. The formation of SN2 products 109 from the cyclic (chlorovinyl)aziridine 107 can be explained by assuming a syn-SN2 ... 

Cyclic vinyloxiranes react with organocuprates with inversion of configuration (anti) and in a vinyl-ogous mode (equation 46), not by the expected Sn2 reaction that simple oxiranes are known to undergo. This subject has recently been summarize. ... 

Nucleophiles like lithium enolates and organocuprates can be added to the terminus of the allyl ligand of cationic cyclic allyl(carbene)iron complexes to give 4-substituted tricarbonyl[l,(3 )-diene]iron complexes. Subsequent to the nucleophilic addition, a ferra-Claisen rearrangement is supposed to be involved in the reaction mechanism. The free dienes can be released by treatment with ceric ammonium nitrate or alkaline hydrogen peroxide (Scheme 4-65). ... 

---