Synthesis of tetrahydrofurans by cyclization of homoallylic alcohols with Iodine/Iodine (III)

RS Vasconcelos, LF Silva Jr…

文献索引：Vasconcelos, Ramon S.; Silva Jr., Luiz F.; Giannis, Athanassios Journal of Organic Chemistry, 2011 , vol. 76, # 5 p. 1499 - 1502

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被引用次数: 17

摘要

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 ...