Published TCIMAIL newest issue No.196
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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.
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Used Chemicals
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Procedure
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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.
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Experimenter’s Comments
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The reaction solution was monitored by UPLC.
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Analytical Data
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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).
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Other References
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- Scalable Synthesis of Biologically Relevant Spirocyclic Pyrrolidines
