Asymmetrische Katalyse durch Vitamin B₁₂: Isomerisierung achiraler 1,4-Epiperoxide zu optisch aktiven 4-Hydroxycycloalk-2-en-1-onen
DOI:
https://doi.org/10.2533/chimia.1991.30Abstract
Achiral cyclic 1,4-epiperoxides undergo fast isomerization to optically active 4-hydroxycycloalk-2-en-1-ones in presence of catalytic amounts of cob(II)alamin (B12r). Light-induced oxygenation of cyclic conjugated dienes in MeOH to 1,4-epiperoxides followed by isomerization with 0,5 mol-% B12 and 5 mol-% vitamin C in the same solvent allows the conversion of cyclohexa-1,3-diene to (S)-4-hydroxycyclohex-2-en-1-one (yield 50%,ee 17%) and of cyclopentadiene to (S)-4-hydroxycyclopent-2-en-1-one (yield 70%, ee = 17.5%) in one pot.
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1991-02-27
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Copyright (c) 1991 Swiss Chemical Society
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How to Cite
[1]
S. Essig, R. Scheffold, Chimia 1991, 45, 30, DOI: 10.2533/chimia.1991.30.