1992年Kennedy, R. M. 等人报道了5-羟基烯烃和氧化铼(VII) (Re₂O₇)反应得到2-羟甲基四氢呋喃的反应。此氧化环化反应是顺式加成，产量稳定，但有少量的醇被氧化为羰基化合物。

尽管此反应有很高的立体选择性，但为了让底物完全反应需要加入多余化学当量的Re₂O_{7。后来改进法加入了另一种氧化剂}H₅IO_{6共同反应，只需要催化量的}Re₂O_{7就可以将5-羟基烯烃氧化为相应的四氢呋喃羟甲基化合物，}

Mechanism

General procedure

化学当量 rhenium (VII) oxide¹.

To a solution of 1 mmol of 5-hydroxyalkenes and 1.1mmol of 2, 6-lutidine in 5 ml of methylene chloride at room temperature wasadded 1.1 mmol of Re₂O_7. The rhenium (VII) oxidedissolved rapidly providing a red solution that gradually yielded a blackprecipitate as the reaction proceeded. After 1 hr, 1.1 mmol of 2, 6-litidinefollowed by 1.1 mmol of rhenium (VII) oxide were added. This sequence wasrepeated again after another hour. After 8 hrs, 10 mmol of sodium hydroperoxidewas added as a 1 M aqueous solution. The resulting colorless mixture wasstirred for 30 minutes, and then diluted with 10 ml of methylene chloride. Theorganic layer was washed with 10 ml of 1 N HCl to remove 2, 6-lutidine followedby 10 ml of saturated NaCl solution. The products were then purified byflashchromatography on silica gel.

催化量rhenium (VII) oxide (Re₂O₇) 和 H₅IO_{6进行反应}².

To a mixture of 1.0 mmol of 5-hydroxyalkene and 1.3mmol of periodic acid (H₅IO₆) in CH₂Cl₂at room temperature, was added 0.5 mmol rhenium (VII) oxide (Re₂O₇).The reaction was    monitored by TLC untilall starting material was consumed (about 15 hr). Then, 10 equivalents of NaHSO₃as 1.0 M aqueous solution was added. After stirring for 30 min, the reactionmixture was diluted with CH₂Cl₂ and the product waspurified in normal fashion.

参考文献

1.       Kennedy, R. M.; Tang, S. TetrahedronLett. 1992, 33, 3729.

2.       Tang, S.; Kennedy, R. M. TetrahedronLett. 1992, 33, 5303.