Tetrahedron

Reductive lithiation of cyclic benzofused ethers: a source of oxygen-functionalised organolithium compounds

M Yus, F Foubelo, JV Ferrández, A Bachki

Index: Yus, Miguel; Foubelo, Francisco; Ferrandez, Jose V; Bachki, Abderrazak Tetrahedron, 2002 , vol. 58, # 24 p. 4907 - 4915

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Citation Number: 17

Abstract

The reaction of 2, 3-dihydrobenzofuran (1) with lithium and a catalytic amount of 4, 4′-di- tert-butylbiphenyl (DTBB, 5%) in THF at 0° C for 1.5 h, followed by addition of an electrophile [E+= H2O, tBuCHO, PhCH2CHO, Ph (CH2) 2CHO, PhCHO, furfural, Me2CO, Et2CO, cyclopentanone, cyclohexanone, cyclooctanone,(−)-menthone] in THF at− 78° C gives, after hydrolysis, compounds 3. Some diols 3 are easily transformed into 2-substituted ...