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Synthesis of Tetrahydrofurans by Cyclization of Homoallylic Alcohols with Iodine/Iodine(III)

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journal contribution
posted on 04.03.2011, 00:00 by Ramon S. Vasconcelos, Luiz F. Silva, Athanassios Giannis
Tetrahydrofuran derivatives can be obtained by cyclofunctionalization of homoallylic alcohols bearing a terminal double bound by using [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser’s reagent) in the presence of a catalytic amount of I2 (20 mol %) in MeOH under mild conditions. This transformation is an overall 5-endo-trig cyclization, which occurs by two different pathways. The first is a 4-exo-trig cyclization followed by ring expansion, whereas the second is an electrophilic addition followed by a 5-endo-tet cyclization.