6-Oxabicyclo[3.1.0]hex-2-ene → Cyclopent-3-en-1-one

HRID 583543Notes

Reaction equation

HRID 583543 reaction equation
[O:1]1[CH:6]2[CH:2]1[CH:3]=[CH:4][CH2:5]2.F[C:8](F)(F)[C:9]([O:11]O)=O>>[C:2]1(=[O:1])[CH2:6][CH:5]=[CH:4][CH2:3]1.[O:11]1[CH:9]2[CH:8]1[CH2:3][C:2](=[O:1])[CH2:6]2

Participants

4

Reactant 2

HCID 1655746-Oxabicyclo[3.1.0]hex-2-eneHCID 10290812Trifluoroperacetic acid

Product 2

HCID 84351Cyclopent-3-en-1-oneHCID 5355326-Oxabicyclo(3.1.0)hexan-3-one

Procedure

The requisite epoxide 211 for the enantioselective ring-opening reaction was prepared according to the method of Noyori (Suzuki, M.; Oda Y., Noyori, R. J. Am. Chem. Soc. 1979, 101, 1623-1625). Thus, 3-cyclopentenone was synthesized via the Pd(0)-catalyzed rearrangement of 3,4-epoxycyclopentene, a reaction remarkable both for the efficiency of catalysis and the ease of the experimental procedure. Epoxidation of 3-cyclopantenone was effected with trifluoroperacetic acid to afford 3,4-epoxycyclopentanone (211) in 60% isolated yield after distillation. We found that treatment of the trifluroacetic anhydride with hydrogen peroxide urea addition compound provided a useful alternative to the literature method for the preparation of trifluoroperacetic acid Noyori's procedure for preparation of trifluoroperacetic acid specifies the use of 90% H2O2. Overall, this two-step sequence provided multigram quantities of epoxide 211 in pure form with no chromatographic purification necessary.

Workup

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Sources & evidence

ORD record
ord-0d562bc47c344db2ad9e1a9d1886551b
Source dataset
uspto-grants-1999_07
Patent number
US05929232

Reaction notes

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