反应详情

温度

-78 °C

(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone (0.348 g, 1.96 mmol) was dissolved in tetrahydrofuran (20 mL) and cooled to −78° C. n-Butyllithium (1.6M in hexanes; 1.64 mL, 2.62 mmol) was added, and the reaction was stirred for 1 hour at −78° C. 2-(4-Bromo-phenyl)-propionyl chloride (0.540 g, 2.18 mmol) in tetrahydrofuran (10 mL) was added, and the reaction was stirred for 30 minutes. The mixture was concentrated, and the residue was partitioned between EtOAc and water. The organic layer was separated, dried, and concentrated, and the crude material was purified by silica gel chromatography (0-25% EtOAc in hexanes) to give two diastereomers as separated products. Diastereomer A was the first product to come off the column, while Diastereomer B was the second product to come off the column.

1. additionwas added
2. stirringthe reaction was stirred for 30 minutes
3. concentrationThe mixture was concentrated
4. customthe residue was partitioned between EtOAc and water
5. customThe organic layer was separated
6. customdried
7. concentrationconcentrated
8. customthe crude material was purified by silica gel chromatography (0-25% EtOAc in hexanes)
9. customto give two diastereomers
10. customas separated products