TCI Practical Example: Hosomi-Sakurai Allylation via an Imine Intermediate

We are proud to present the three component reaction with the Hosomi-Sakurai allylation reaction using allyl(trimethyl)silane.

Used Chemicals

Procedure: Cyclopentanone (890 µL, 10 mmol), benzyl carbamate (1.81 g, 12 mmol) and allyltrimethylsilane (2.2 mL, 14 mmol) were dissolved in dichloromethane (14 mL). After cooling to 0 °C, BF₃·Et₂O (1.51 mL, 12 mmol) was added and the reaction mixture was stirred for 21 hours at room temperature. After the reaction, the mixture was washed with satd. NaHCO₃ aq. (10 mL), brine (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane:ethyl acetate = 9:1) to afford benzyl (1-allylcyclopentyl)carbamate (1.84 g, 71% yield) as a clear yellow liquid.

Analytical Data

Benzyl (1-Allylcyclopentyl)carbamate

¹H NMR (400 MHz, CDCl₃); δ 7.35-7.29 (m, 5H), 5.82-5.72 (m, 1H), 5.06-5.02 (m, 4H), 4.68 (brs, 1H), 2.52-2.51 (m, 2H), 1.76-1.61 (m, 8H).

Other References