Cyclohexanone → 2-Cyclohepten-1-one

HRID 735288

Reaktionsgleichung

Reaktionsgleichung von HRID 735288
[C:1]1(=[O:6])[CH2:5][CH2:4][CH:3]=[CH:2]1.[C:7]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>>[C:1]1(=[O:6])[CH2:5][CH2:4][CH2:3][CH2:2][CH:8]=[CH:7]1.[C:7]1(=[O:13])[CH2:2][CH2:1][CH2:8][CH2:9][CH2:10][CH:11]=[CH:12]1.[CH:5]1[C:1](=[O:6])[CH2:5][CH2:1][CH2:2][CH2:3][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:7][CH2:2][CH2:3][CH:4]=1

Komponenten

5

Edukt 2

HCID 7967CyclohexanoneHCID 135882-Cyclopenten-1-one

Produkt 3

HCID 707232-Cyclohepten-1-oneHCID 137176Cyclooctene-3-oneHCID 540403452-Cyclopentadecenone

Versuchsvorschrift

As may be seen in the table, cyclopentenone and cyclohexanone provided for modest enantiocontrol (12-15:1 endo:exo, 48-63% ee, 81% yield), while cycloheptenone (n=2), cyclooctenone (n=3), and (E) cyclopentadecene-2-one (n=10) were found to be highly enantioselective (entries 3-5, 5-18:1 endo:exo, 90-93% ee, 83-88% yield). Cyclopentenone (n=0, entry 1) and cyclohexanone (n=1, entry 2) were found to be somewhat less enantioselective.

Quellen und Nachweise

ORD-Eintrag
ord-0887465990e24916920d9fc6847df7fe
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592463B2

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