Partial separation of enantiomeric 1,2-diols via ketal formation with a polymer-supported chiral ketone

Clarke, Ian D.; Hodge, Philip

doi:10.1039/a702567j

Cited by 7 publications

(3 citation statements)

References 10 publications

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“…13,14 The binary phase diagram for the trans-1,2-cyclohexanediol 1 enantiomers was determined by Leitão et al 15 Several publications can be found in the literature dealing with the chiral derivatization or resolution of racemic trans-1,2-cyclohexanediol. [16][17][18][19][20][21] In a few cases, high enantiomeric purity was achieved. Lainé et al resolved racemic trans-1,2-cyclohexanediol via the formation of dispiroketals.…”

Section: Introductionmentioning

confidence: 97%

Resolution of racemic trans-1,2-cyclohexanediol with tartaric acid

Molnar

Thorey²,

Bánsághi³

et al. 2008

Tetrahedron: Asymmetry

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Section: Introductionmentioning

confidence: 97%

Resolution of racemic trans-1,2-cyclohexanediol with tartaric acid

Molnar

Thorey²,

Bánsághi³

et al. 2008

Tetrahedron: Asymmetry

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“…Previous enantioseparations of the racemic cyclohexanediol, performed not only for analytical purposes, fail to produce both of the pure enantiomers. − We propose a novel procedure in which both enantiomers are produced in high purity while reuse of the resolving agent is also straightforward.…”

Section: Introductionmentioning

confidence: 99%

Environmentally Benign Chiral Resolution of trans-1,2-Cyclohexanediol by Two-Step Supercritical Fluid Extraction

Székely

Bánsághi

Thorey

et al. 2010

Ind. Eng. Chem. Res.

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A racemic mixture of trans-1,2-cyclohexanediol (CHD) is reacted with S,S-or R,R-tartaric acid in ethanol with a 0.5 or higher molar ratio of resolving agent to racemic CHD. The tartaric acid (TA) forms a diastereomeric cocrystal with only one of the enantiomers; the other enantiomer remains unreacted at any molar ratio. The unreacted mixture of enantiomers is recovered from the sample by supercritical fluid extraction at 20 MPa and 33 °C. A subsequent extraction is then performed at 20 MPa and at least 73 °C. During this second extraction step, the diastereomeric cocrystal is decomposed in situ. Both enantiomers are recovered in nearly 50-50% yield with enantiomeric excess values of 65-90%. The mixtures of enantiomerss rich in S,S-CHD and R,R-CHD are then reacted with S,S-TA and R,R-TA, respectively, and the procedure is repeated. In two resolution steps, both enantiomers of CHD were produced in quantitative yields in a purity of ee > 99%.

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“…Other recently reported functional group manipulations include the conversion of an amide to a thioamide on functionalised polystyrene resin, 153 and acetal formation between racemic chiral diols and a polymer supported 7-ketosteroid 141 (Scheme 62). 154…”

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confidence: 99%