| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1350408 | Tetrahedron: Asymmetry | 2007 | 7 Pages |
An efficient enantioselective synthesis of curcumene and curcuphenol is described. The key intermediates, substituted butanoates 7a and 7b and their acids 8a and 8b are obtained in high enantiopurity (>99% ee) by a lipase-catalyzed kinetic resolution process. The enantiopure intermediates thus obtained were utilized for the total synthesis of the target compounds.
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(3R)-Ethyl 3-(4-methylphenyl)butanoateC13H18O2[α]D25=-26.2 (c 3.5, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (3R)
(3R)-Ethyl 3-(2-methoxy-4-methylphenyl)butanoateC14H20O3[α]D25=-2.7 (c 1.0, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (3R)
(3S)-3-(4-Methylphenyl)butanoic acidC11H14O2[α]D25=+34.2 (c 1.0, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (3S)
(3S)-3-(2-Methoxy-4-methylphenyl)butanoic acidC12H16O3[α]D25=+16.2 (c 2.5, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (3S)
(3S)-3-(4-Methylphenyl)-1-butanolC11H16O[α]D25=+30.1 (c 1.0, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (3S)
(3S)-3-(2-Methoxy-4-methylphenyl)-1-butanolC12H18O2[α]D25=+21.6 (c 1.0, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (3S)
(3S)-3-(4-Methylphenyl)butyl 4-methyl-1-benzenesulfonateC18H22O3S[α]D25=+37.7 (c 1.0, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (3S)
(3S)-3-(2-Methoxy-4-methylphenyl)butyl 4-methyl-l-benzenesulfonateC19H24O4S[α]D25=+14.2 (c 3.6, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (3S)
(6S)-2-Methyl-6-(4-methylphenyl)-2-hepteneC15H22[α]D25=+42.7 (c 1.0, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (6S)
(6S)-6-(2-Methoxy-4-methylphenyl)-2-methyl-2-hepteneC16H24O[α]D25=+7.1 (c 1.0, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (6S)
2-[(1S)-1,5-Dimethyl-4-hexenyl]-5-methylphenolC15H22O[α]D25=+23.5 (c 1.0, CHCl3)Source of chirality: enzymatic resolutionAbsolute configuration: (1S)
