Cyclopropanation of alkenes with CH2I2/Et3Al by the phase-vanishing method based on fluorous phase screen

Phase-vanishing (PV) method using perfluorohexanes as a screen phase was applied to cyclopropanation reactions with CH2I2/Et2Zn and CH2I2/Et3Al. When Et3Al was used as a carbenoid generator, the reaction proceeded smoothly and desired cyclopropane derivatives were obtained in high yield. The PV cyclopropanation took 2 or 3 days to complete, however, reduction of reaction time by a factor of 2–3 was also achieved by vigorous stirring after the bottom CH2I2 layer disappeared.

Cyclopropanation reactions with the Maruoka–Yamamoto reagent (Et3Al/CH2I2) were carried out successfully using fluorous media as a phase screen. Figure optionsDownload as PowerPoint slide