Long-range exciton coupling from dipyrrinone chromophores

A novel family of chiral acylation catalysts based on a N-4'-pyridinyl-alpha-methyl proline structure has been studied. A set of 31 compounds has been easily prepared and screened in the kinetic resolution of racemic alcohol 33 resulting in high enantioselectivities in most cases. From results obtained, H-bonding interactions between the catalyst and the substrate would appear essential to afford high enantioselectivity during the catalytic acylation. Additional solvent dependence and anhydride studies have been made to better identify the mechanism. This work has been further extended to the study of a number of structurally different alcohols. Ethanolamine derivatives in particular were found to be highly effective substrates (up to S = 18.8) in the kinetic resolution.

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“…Physicochemical characterization of alcohols 34 , 38 , and 39 7 has been previously described in the literature.…”

Section: Methodsmentioning

confidence: 99%

The Design of NovelN-4‘-Pyridinyl-α-methyl Proline Derivatives as Potent Catalysts for the Kinetic Resolution of Alcohols

et al. 2003

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ChemInform Abstract: Long‐Range Exciton Coupling from Dipyrrinone Chromophores.

Byun

Lightner

1992

ChemInform

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Exciton chirality in trans‐1,2‐diamidocyclohexanes: Fluorescent chromophores

Boiadjiev

Lightner

2005

Chirality

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N,N'-Carbonyl-bridged dipyrrinones constitute a new class of highly fluorescent chromophores suitable for investigations of stereochemistry and absolute configuration. Xanthoglow (N,N'-carbonylxanthobilirubic acid) diamides of trans-1,2-diaminocyclohexane are strongly fluorescent (phiF=0.37, lambdaem=500 nm, lambdaex=419 nm in CHCl3) but exhibit only weak exciton circular dichroism (CD). In contrast, the diamide of (1R,2R)-diaminocyclohexane from the xanthoglow analogue whose propionic acid has been replaced by benzoic acid (N,N'-carbonyl-8-(4-carboxyphenyl)-3-ethyl-2,7,9-trimethyl-(10H)-dipyrrin-1-one) exhibits even stronger fluorescence (phiF=0.62, lambdaem=495 nm, lambdaex=422 nm in CHCl3) and UV-visible absorption (epsilon=41,600 dm3.mol-1.cm-1 at 424 nm) in organic solvents. Its exciton CD (Deltaepsilon=-13 dm3.mol-1.cm-1, lambda=432 nm; Deltaepsilon=+2 dm3.mol-1.cm-1, lambda=382 nm) correlates with the exciton chirality rule.

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Long-range exciton coupling from dipyrrinone chromophores

Cited by 10 publications

References 27 publications

The Design of NovelN-4‘-Pyridinyl-α-methyl Proline Derivatives as Potent Catalysts for the Kinetic Resolution of Alcohols

The Design of NovelN-4‘-Pyridinyl-α-methyl Proline Derivatives as Potent Catalysts for the Kinetic Resolution of Alcohols

ChemInform Abstract: Long‐Range Exciton Coupling from Dipyrrinone Chromophores.

Exciton chirality in trans‐1,2‐diamidocyclohexanes: Fluorescent chromophores

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