Abstract
Protected alpha-formyl amino acids, themselves available from the corresponding alpha-vinyl amino acids, are stereoselectively transformed into the (Z)-configured alpha-(2'-fluoro)vinyl amino acids via a three-step sequence. The route employs McCarthy's reagent, diethyl alpha-fluoro-alpha-(phenylsulfonyl)methyl phosphonate, and proceeds via the intermediate (E)-alpha-fluorovinyl sulfones and (E)-alpha-fluorovinylstannanes. The latter may either be exploited as novel cross-coupling partners for fluorovinyl branch extension or be globally deprotected, to provide the title compounds. [structure: see text]
Publication types
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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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Amino Acids / chemical synthesis*
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Amino Acids / chemistry*
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Amino Acids / pharmacology
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Aromatic Amino Acid Decarboxylase Inhibitors*
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Aromatic-L-Amino-Acid Decarboxylases / metabolism
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Fluorine / chemistry
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Stereoisomerism
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Sulfones / chemistry
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Tin Compounds / chemistry
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Vinyl Compounds / chemical synthesis
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Vinyl Compounds / chemistry*
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Vinyl Compounds / pharmacology
Substances
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Amino Acids
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Aromatic Amino Acid Decarboxylase Inhibitors
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Sulfones
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Tin Compounds
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Vinyl Compounds
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stannane
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Fluorine
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Aromatic-L-Amino-Acid Decarboxylases