Direct separation of carboxylic acid enantiomers by high-performance liquid chromatography with amide and urea derivatives bonded to silica gel as chiral stationary phases

Ôi, Naobumi; Kitahara, Hajimu; Aoki, Fumiko; Kisu, Naoko

doi:10.1016/0021-9673(94)00890-l

Cited by 50 publications

(5 citation statements)

References 10 publications

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“…In the past decades, several chromatographic resolutions of chrysanthemic acid and its analogues have been reported. For example, the direct resolutions of chrysanthemic acid have been achieved on the brush‐type CSPs derived from (+)‐terguride alkaloid,2, 3 amino acids,4 tripeptide esters,5 and cinchona alkaloid derivatives 6. Recently, the effectiveness of the polysaccharide‐based CSPs, Chiralcel OD, Chiralcel OF, and Chiralpak AS, for the resolution of the underivatized chrysanthemic acid has been reported 7, 8.…”

Section: Introductionmentioning

confidence: 99%

Preparation of HPLC chiral packing materials using cellulose tris(4‐methylbenzoate) for the separation of chrysanthemate isomers

Yamamoto

Yamada

Motoya

et al. 2006

J. Polym. Sci. A Polym. Chem.

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We investigated the separation of chrysanthemate isomers (1), particularly the (1R)-trans form, by high-performance liquid chromatography (HPLC) using polysaccharide derivatives, such as the phenylcarbamates and benzoates of cellulose and amylose, as the chiral stationary phases (CSPs). The chiral packing materials (CPMs) having a high chiral recognition for the chrysanthemic acid ethyl ester (1a) were prepared by coating cellulose tris(4-methylbenzoate) (2a) dissolved in solvents containing methyl benzoate or acetophenone as an additive on silica gel. The separation factor for 1a significantly depended on the preparation conditions of CPM 2a, such as the coating amount of 2a and the type and amount of additives. The chiral recognition ability created by imprinting the additives was lost when the CPM was heated at a high temperature, and was recovered by contacting it with the additive in a packed column. The structural change in 2a during these treatments was not clearly detected by spectroscopic methods.

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Section: Introductionmentioning

confidence: 99%

Preparation of HPLC chiral packing materials using cellulose tris(4‐methylbenzoate) for the separation of chrysanthemate isomers

Yamamoto

Yamada

Motoya

et al. 2006

J. Polym. Sci. A Polym. Chem.

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“…Consequently, we were delighted to find that a chiral column loaded with ( R )-1-naphthylglycine succeeded in separating the two stereoisomers of (+) 300 /(−) 300 - 10d ( Fig. 4 B ) ( 28 ). Preliminary theoretical investigations on the rotational barrier indicated the presence of a high barrier of >30 kcal ⋅ mol −1 .…”

Section: Resultsmentioning

confidence: 99%

A minimal cage of a diamond twin with chirality

Fukunaga

Kato

Ikemoto

et al. 2022

Proc. Natl. Acad. Sci. U.S.A.

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A network of tetrahedral vertices can fill three-dimensional (3D) spaces in a beautiful and isotropic manner, which is found as diamonds with sp3-hybridized carbon atoms. Although a network of trigonal vertices (i.e., another form of carbon atoms with sp2-hybridization) naturally results in a lower-dimensional two-dimensional network of graphenes, an isotropic 3D arrangement of trigonal vertices has been of theoretical and mathematical interest, which has materialized as a proposal of a “diamond twin.” We herein report the synthesis and optical resolution of a minimal cage of a chiral diamond-twin network. With triangular phenine units at 14 vertices, triply fused decagonal rings were assembled by forming 15 biaryl edges via coupling. A unique chirality of the network has been disclosed with the minimal cage, which may stimulate explorations of chiral carbonaceous materials.

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“…However, CE has precision problem in the migration times with runs compared to HPLC and GC. Many chiral stationary phases available for direct enantioseparation of profens by HPLC require prior derivatization [10][11][12]. In contrast, chiral mobile phase additives provide direct enantioseparation of profens as diastereomeric ion-pairs without derivatization [13,14].…”

Section: Introductionmentioning

confidence: 99%

Chiral discrimination of multiple profens as diastereomeric (R)-(+)-1-phenylethylamides by achiral dual-column gas chromatography

Paik

Lee

Goto

et al. 2004

Journal of Chromatography B

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Direct separation of carboxylic acid enantiomers by high-performance liquid chromatography with amide and urea derivatives bonded to silica gel as chiral stationary phases

Cited by 50 publications

References 10 publications

Preparation of HPLC chiral packing materials using cellulose tris(4‐methylbenzoate) for the separation of chrysanthemate isomers

Preparation of HPLC chiral packing materials using cellulose tris(4‐methylbenzoate) for the separation of chrysanthemate isomers

A minimal cage of a diamond twin with chirality

Chiral discrimination of multiple profens as diastereomeric (R)-(+)-1-phenylethylamides by achiral dual-column gas chromatography

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