反应详情

温度

22.5 °C

(S)-4-Isopropyl-2-[(S)-2-(diphenylphosphino)ferrocen-1-yl]oxazoline (18.8 mg, 0.039 mmol) and Cu(MeCN)4PF6 (14.5 mg, 0.039 mmol) were added to a dried, nitrogen swept reaction vessel. Anhydrous, degassed, BHT inhibited THF (5.0 mL) was then added and the mixture was stirred for 30 minutes at 20-25° C. The resulting solution was then cooled to −78° C. and a solution of 1-(4-[2-fluorobenzyloxy]phenyl)-2-propen-1-one (P4, 2.0 g, 7.80 mmol) and ethyl N-(diphenylmethylidene)glycinate (2.29 g, 8.58 mmol) in THF (15 mL total volume) was added over 1-2 minutes. After 3-5 minutes, a solution of DBU (5.9 mg, 0.039 mmol) in THF (0.5 mL total volume) was added. The solution was then stirred for 8-12 hours at −78° C. The reaction mixture was then warmed to 0-5° C. and 1 M H2SO4 (aq., 25 mL) was then added. The reaction mixture was then warmed to 20-25° C. and mixed vigorously for 2 hours. The mixture was then poured into a rapidly stirring solution of NaHCO3 (saturated, enough to bring the pH to 7.0). After 5 minutes of stirring, the mixture was extracted twice with TBME and the organic extracts were pooled, dried over Na2SO4, and concentrated to near dryness. The resulting residue was purified by flash column chromatography eluting with 0→40% acetone/hexanes (gradient). Concentration of the fractions containing the title compound gave a crystalline solid (2.23 g, 84% yield).

1. customreaction vessel
2. customAnhydrous, degassed
3. additionwas then added
4. temperatureThe resulting solution was then cooled to −78° C.
5. waitAfter 3-5 minutes
6. stirringThe solution was then stirred for 8-12 hours at −78° C
7. temperatureThe reaction mixture was then warmed to 0-5° C.
8. temperatureThe reaction mixture was then warmed to 20-25° C.
9. additionmixed vigorously for 2 hours
10. stirringAfter 5 minutes of stirring
11. extractionthe mixture was extracted twice with TBME
12. dry with materialdried over Na2SO4
13. concentrationconcentrated
14. customThe resulting residue was purified by flash column chromatography
15. washeluting with 0→40% acetone/hexanes (gradient)
16. additionConcentration of the fractions containing the title compound