γ-Lithioalkoxides via Reductive Lithiation of Oxetanes by Aromatic Radical Anions

Article abstract of DOI:10.1021/jo00285a008

Oxetanes are cleaved at 0 deg C in tetrahydrofuran by lithium 4,4'-di-tert-butylbiphenylide, giving lithium γ-lithioalkoxides which can provide 2-substituted tetrahydrofurans by trapping with aldehydes and ketones followed by acid cyclization of the resulting 1,4-diols; the cuprates of these dianions undergo conjugate addition and nucleophilic substitution reactions.