Substituted Epoxides by Lithiation of Terminal Epoxides

Diamine-ligand-assisted direct hydrogen−lithium exchange allows the generation of nonstabilized (H-substituted) oxiranyllithium species and their subsequent trapping by Bu3SnCl and carbonyl-based electrophiles. This reaction provides a new concise route to α,β-epoxystannanes and substituted epoxides.