Structural optimization of a chiral selector for use in preparative enantioselective chromatography

Pirkle, William H.; Koscho, Michael E.

doi:10.1016/s0021-9673(99)00222-8

Cited by 35 publications

(17 citation statements)

References 7 publications

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“…) Chiral stationary phase FUSE-4 was made from an analogue of Betti amine ((2-(Methoxynaphthalen-1-yl)benzylamine) according to an earlier described procedure[15], resolved with d-malic acid[15], and immobilized as carboxamide of 2,2-dimethylpent-4-enoic acid by a previously described method[16] 2. ) Chiral stationary phase FUSE-3 was prepared from commercially available ()-(R)-1-(2-Naphthyl)ethylamine (Lancaster) and immobilized as carboxamide of 2,2-dimethylpent-4-enoic acid by a previously described method[15].…”

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Enantioselective Nucleophilic Aromatic Substitution with Small-Molecule Chiral Selectors

Snyder

Shvets

Pirkle

2002

HCA

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Dedicated to Professor Dieter Seebach on the occasion of his 65th birthday Small-molecule rationally designed chiral selectors have been shown to influence the stereochemical outcome of a variety of organic transformations. For instance, in a recent report, we demonstrated that a chiral selector (in conjunction with an achiral phase-transfer catalyst) could selectively inhibit one enantiomer of electron-deficient aromatic amides from forming Meisenheimer adducts (Scheme 2). We now extend this methodology to performing enantioselective nucleophilic aromatic substitutions. Initial studies involved biphasic kinetic resolutions with a chiral selector in conjunction with an achiral phase-transfer catalyst (Scheme 3). The results are consistent with previous data taken for biphasic reactions (e.g., Scheme 1) where the chiral selector effectively shields the more highly complexed enantiomer from reaction. With neutral nucleophiles such as amines, the enantioselective nucleophilic aromatic substitutions can also be conducted in single-phase systems. Several examples are given.

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Enantioselective Nucleophilic Aromatic Substitution with Small-Molecule Chiral Selectors

Snyder

Shvets

Pirkle

2002

HCA

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“…On the basis of the same principle, Pirkle and Koscho prepared a proline-based CSP ( Fig. 3.19), which was specifically designed for the preparative separation of the enantiomers of two chiral selectors [138]. 3.6.2.4 Combinatorial approach to optimise CSPs For the preparation of tailor-made CSPs, a new approach based on the combinatorial concept has recently been evaluated by different groups [139][140][141][142][143][144].…”

Section: Concept Of Reciprocality For Designing Cspsmentioning

confidence: 99%

Chiral Stationary Phases for Preparative Enantioselective Chromatography

Francotte¹

2005

Preparative Enantioselective Chromatography

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“…Selim [6] separated a series of enantiomers of a dimethyl N-3,5-dinitrobenzoyl-(-amino-substituted benzyl phosphonate derivative on an (R)-2,2,2-trifluoro-1-(9-anthryl)ethanol derivatized chiral stationary phase. Pirkle also reported separation of the enantiomers of a variety of N-DNB-aminophosphonic acid derivatives on the same phase [7] and on (R)-N-(2-naphthyl)-D-alanine [8,9], (S)-N-(1-naphthyl)leucine [9,10], and N- [11-(dimethylethoxysilyl)undecanoyl]-L-proline-3,5-dimethylanilide [11,12]. The enantiomers of several 3,5-dinitrobenzyloxycarbonylaminophosphonic acid derivatives have also been successfully resolved on the quinine carbamate CSP [13].…”

Section: Introductionmentioning

confidence: 99%

Effect of the structure of organic phosphonate compounds on chiral separations on derivatized cellulose chiral stationary phase

Yang

Zhou

et al. 2002

Chromatographia

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Key WardsColumn liquid chromatography Chiral stationary phase Chiral separation Organic phosphonate compounds SummaryThe enantiomers of eight O,O-dialkyl-2-benzyloxycarbonylaminoarylmethyl phosphonates have been directly separated on a tris(3,5-dimethylphenylcarbamate) cellulose column. The results are very different from those obtained by separation on an N-(3,5-dinitrobenzoyl)leucine (DNBleu) column. The effect of mobile phase composition and column temperature on retention and enantioselectivity were investigated. The effect on chiral separation of the length of, and steric hindrance by, alkoxyl groups of the phosphonate ester and of the nature of the substituents p-CI and p-H on the benzene ring attached to the chiral carbon atom are also discussed.

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Structural optimization of a chiral selector for use in preparative enantioselective chromatography

Cited by 35 publications

References 7 publications

Enantioselective Nucleophilic Aromatic Substitution with Small-Molecule Chiral Selectors

Enantioselective Nucleophilic Aromatic Substitution with Small-Molecule Chiral Selectors

Chiral Stationary Phases for Preparative Enantioselective Chromatography

Effect of the structure of organic phosphonate compounds on chiral separations on derivatized cellulose chiral stationary phase

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