Abstract
A short and efficient synthesis of homopentafluorophenylalanine (6) from oxazolidine aldehyde 1 in 57% overall yield and in > 98% ee is described. The enantiomeric excess of the product was determined by 19F NMR analysis of the coupling product derived from 5 and L-Ser(O-t-Bu)-OCH3, by comparison to a dipeptide obtained from racemic 5.
Copyright 2004 American Chemical Society
Publication types
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Comparative Study
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Catalysis
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Dipeptides / chemistry
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Electrochemistry
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Hydrocarbons, Fluorinated / analysis
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Hydrocarbons, Fluorinated / chemical synthesis*
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Phenylalanine / analogs & derivatives*
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Phenylalanine / analysis
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Phenylalanine / chemical synthesis*
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Stereoisomerism
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Toluene / analogs & derivatives
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Toluene / chemistry
Substances
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Dipeptides
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Hydrocarbons, Fluorinated
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Toluene
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Phenylalanine