Practical Synthesis of Enantiomerically Pure 2-(Diphenylphosphanyl)ferro­cene Carboxylic Acid

Bernhard Breit; Daniel Breuninger

doi:10.1055/s-2005-872111

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Practical Synthesis of Enantiomerically Pure 2-(Diphenylphosphanyl)ferrocene Carboxylic Acid

Bernhard Breit*, Daniel Breuninger
Institut für Organische Chemie und Biochemie, Albert-Ludwigs-Universität Freiburg, Albertstr. 21, 79104 Freiburg, Germany
Fax: +49(761)2038715; e-Mail: bernhard.breit@organik.chemie.uni-freiburg.de;

Abstract

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Abstract

A practical synthesis of both enantiomers of ortho-diphenylphosphanylferrocene carboxylic acid (o-DPPFA) starting from ferrocene is described. Key steps include the synthesis of the racemic title compound from ferrocene in two steps followed by resolution by way of diastereomeric ester formation with glucose diacetonide. The synthesis allows for preparation of gram quantities of both optical antipodes of o-DPPFA (3) in good yields and enantiomerically pure form (>99% ee).

Key words

metallocenes - asymmetric synthesis - synthetic methods - enantiomeric resolution - phosphorus

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Practical Synthesis of Enantiomerically Pure 2-(Diphenylphosphanyl)ferro­cene Carboxylic Acid

Practical Synthesis of Enantiomerically Pure 2-(Diphenylphosphanyl)ferrocene Carboxylic Acid