Synthesis, characterization and resolution of racemic (2-methylsulfinyl)phenylphosphonic acid methyl ester via its cinchoninium salts

The synthesis of new (2-methylsulfinyl)phenylphosphonic acid methyl and dimethyl esters in both racemic and non-racemic forms is reported. Resolution of the racemic phosphonic acid mono-ester 1 was accomplished via diastereomeric salt formation with cinchonine. The absolute stereochemistry of the ph...

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Published in:Tetrahedron: asymmetry 2001-02, Vol.12 (1), p.167-174
Main Authors: Mauger, Christelle, Masson, Serge, Vazeux, Michel, Saint-Clair, Jean-François, Midura, Wanda H., Drabowicz, Josef, Mikolajczyk, Marian
Format: Article
Language:English
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Summary:The synthesis of new (2-methylsulfinyl)phenylphosphonic acid methyl and dimethyl esters in both racemic and non-racemic forms is reported. Resolution of the racemic phosphonic acid mono-ester 1 was accomplished via diastereomeric salt formation with cinchonine. The absolute stereochemistry of the phosphonic ester products was deduced from asymmetric sulfoxidation experiments and confirmed by chemical correlation with ( S)-(−)-2-methylsulfinylaniline. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(01)00008-8