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

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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17

The quality of both s-BuLi and chlorodiphenylphosphine was crucial to obtain good results. Older solutions of s-BuLi often led to dramatically decreased yields (ca. 30%).