| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346403 | Tetrahedron: Asymmetry | 2011 | 6 Pages |
The aerobic oxidative kinetic resolution of racemic α-hydroxy ketones was accomplished using a chiral Zn–quinine complex as the catalyst in the presence of molecular oxygen. The resulting optimized reaction conditions were applied to resolute different types of racemic α-hydroxy ketones and a maximum of 9.2 selectivity (s) was obtained with 88% ee for the recovered α-hydroxy ketone.
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(S)-2-Hydroxy-1,2-diphenylethanoneC14H12O2Ee = 55%[α]D25=+44.2 (c 1.0, acetone)Source of chirality: oxidative kinetic resolutionAbsolute configuration: (S)
(S)-1,2-Bis(4-bromophenyl)-2-hydroxyethanoneC14H10Br2O2Ee = 88%[α]D25=+9.1 (c 1.0, MeOH)Source of chirality: oxidative kinetic resolutionAbsolute configuration: (S)
(S)-2-Hydroxy-1,2-di-p-tolylethanoneC16H16O2Ee = 50%[α]D25=+79.2 (c 1.0, MeOH)Source of chirality: oxidative kinetic resolutionAbsolute configuration: (S)
(S)-1,2-Bis(4-ethylphenyl)-2-hydroxyethanoneC18H20O2Ee = 52%[α]D25=+41.3 (c 1.0, MeOH)Source of chirality: oxidative kinetic resolutionAbsolute configuration: (S)
(S)-2-(4-Chlorophenyl)-2-hydroxy-1-phenylethanoneC14H11ClO2Ee = 29%[α]D25=+24.8 (c 1.0, MeOH)Source of chirality: oxidative kinetic resolutionAbsolute configuration: (S)
(S)-2-Hydroxy-1,2-di-m-tolylethanoneC16H16O2Ee = 36%[α]D25=+49.4 (c 1.0, MeOH)Source of chirality: oxidative kinetic resolutionAbsolute configuration: (S)
(S)-2-Hydroxy-1,2-di-o-tolylethanoneC16H16O2Ee = 41%[α]D25=+47.5 (c 0.5, MeOH)Source of chirality: oxidative kinetic resolutionAbsolute configuration: (S)
(S)-2-Hydroxy-1,2-di(naphthalen-2-yl)ethanoneC22H16O2Ee = 22%[α]D25=+10.4 (c 1.0, MeOH)Source of chirality: oxidative kinetic resolutionAbsolute configuration: (S)
(S)-2-Hydroxy-1,2-bis(3-methoxyphenyl)ethanoneC16H16O4Ee = 30%[α]D25=+17.8 (c 1.0, acetone)Source of chirality: oxidative kinetic resolutionAbsolute configuration: (S)
