Metal-mediated enantioselective access to unfunctionalized aliphatic oxiranes: prochiral and chiral recognition

Schurig, Volker; Betschinger, F.

doi:10.1021/cr00013a006

Cited by 153 publications

(48 citation statements)

References 53 publications

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“…5). 25 Below T isoenant , the (S)-enantiomer, which forms a stronger bond to nickel(II), is eluted as the second peak but above T isoenant is eluted as the first peak! At 90jC only one peak is observed.…”

Section: Quantitation Of Enantioselectivity By the Concept Of The Retmentioning

confidence: 99%

“…ref. 25). These advances were considered as predecessors of the well-known titanium/tartrate system (Katsuki -Sharpless epoxidation) 26 and the manganese(II) -salen system (Jacobsen kinetic resolution).…”

Section: Extension Of the Scope Of Enantioselective Complexation Gc Tmentioning

confidence: 99%

“…48 The latter program is currently also used for reaction chromatography. Many examples featuring enantiomerization in complexation GC have been investigated, e.g., for 1,6 -dioxaspiro [4.4]nonane, 22 phenyloxirane, 25 isopropenyloxirane, 25 and homofuran. 49 For homofuran a perfect agreement between experimental and simulated chromatograms was obtained (cf.…”

Section: Peak Profiles Due To Enantiomerization; Access To Kinetic Acmentioning

confidence: 99%

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Contributions to the theory and practice of the chromatographic separation of enantiomers

Schurig

2005

Chirality

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The theory and practice of enantioselective capillary chromatography employing metal coordination compounds and modified cyclodextrins as chiral stationary phases are treated. A unified approach involving all contemporary chromatographic methods and a single enantioselective column is described. Reliable thermodynamic data of enantioselectivity are derived by the retention-increment method. The existence of an isoenantioselective temperature is demonstrated. Kinetic enantiomerization studies are presented. The preparative-scale separation of enantiomers by gas chromatography with enantioselective packed columns is achieved. Unusual phenomena and future aspects of enantioselective chromatography are discussed.

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Section: Quantitation Of Enantioselectivity By the Concept Of The Retmentioning

confidence: 99%

Section: Extension Of the Scope Of Enantioselective Complexation Gc Tmentioning

confidence: 99%

Section: Peak Profiles Due To Enantiomerization; Access To Kinetic Acmentioning

confidence: 99%

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Contributions to the theory and practice of the chromatographic separation of enantiomers

Schurig

2005

Chirality

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“…The distribution of enantiomers A and B between mobile phase (mob) and the stationary phase (stat) is determined according to Eqs. [1] and [2]:…”

Section: Theoretical Aspects Enantioselective Dynamic Chromatographymentioning

confidence: 99%

“…The chiral recognition between the racemic selectand and the nonracemic selector is the prerequisite for a successful separation of enantiomers. However, this goal is not met when only one peak is observed [1][2][3][4] as the result of as many as six coalescence phenomena which may occur in enantioselective chromatography. 3,4 Peak coalescence of the first kind is associated with an unresolved peak observed for a racemic selectand due to a negligible enantioselectivity of the nonracemic selector (−⌬ D,L ⌬G < 0.025 kJ/mol (25°C), ␣ < 1.01).…”

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Determination of enantiomerization barriers by dynamic and stopped‐flow chromatographic methods

2001

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In recent years, dynamic chromatography and stopped-flow chromatographic techniques have become versatile tools for the determination of enantiomerization and isomerization barriers. Increasing demands for the stereochemical safety of chiral drugs contributed to the rapid development of new techniques. New computer-aided evaluation systems allow the on-line determination of interconversion barriers from the experimental chromatograms. Both dynamic chromatography and stopped-flow chromatography have been applied to the entire range of chromatographic methods (GC, SFC, HPLC, CE).

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Reactivity of oxiranes with organolithium reagents

Chemla

Vrancken

2004

The Chemistry of Organolithium Compounds

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Metal-mediated enantioselective access to unfunctionalized aliphatic oxiranes: prochiral and chiral recognition

Cited by 153 publications

References 53 publications

Contributions to the theory and practice of the chromatographic separation of enantiomers

Contributions to the theory and practice of the chromatographic separation of enantiomers

Determination of enantiomerization barriers by dynamic and stopped‐flow chromatographic methods

Reactivity of oxiranes with organolithium reagents

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