Abstract
Dipeptides obtained from l-proline and beta(3)-l-amino acids are reported to catalyze enantioselective direct aldol reaction in aqueous medium, leading to significant anti:syn diastereomeric ratios and enantiomeric excesses. The simple introduction of a polar substituent at the C-2 position of the beta(3)-l-amino acid was also found to enhance appreciably both diastereo- and enantioselectivity of the catalyst.
MeSH terms
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Aldehydes / chemistry*
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Benzaldehydes / chemistry
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Catalysis
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Chromatography, High Pressure Liquid
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Cyclohexanones / chemistry
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Dipeptides / chemistry*
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Esters / chemistry*
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Hydrophobic and Hydrophilic Interactions
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Magnetic Resonance Spectroscopy
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Proline / analogs & derivatives
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Proline / chemistry*
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Stereoisomerism
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Tryptophan / analogs & derivatives
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Tryptophan / chemistry
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Tyrosine / analogs & derivatives
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Tyrosine / chemistry
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Water / chemistry*
Substances
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Aldehydes
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Benzaldehydes
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Cyclohexanones
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Dipeptides
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Esters
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Water
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Tyrosine
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4-nitrobenzaldehyde
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cyclohexanone
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3-hydroxybutanal
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Tryptophan
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Proline