Sulfoxide sulindac, chiral

This methodology has been successfully applied to the asymmetric synthesis of (R)- and (S)-sulindac (90-92% ee), which is a chiral sulfoxide marketed as an antiinflammatory drug (Scheme 3.54) [165],... 

Other oxidoreduction examples of inversion are the sulfoxide/sulfide and N-oxide/tertiary amine equihbria. Chiral sulfoxides (e.g., sulindac, flosequinan, pantoprazole) that contain tricoordinated sulfur atoms or tertiary amine N-oxides are first reduced by reductases to the corresponding achiral sulfides or tertiary amines, respectively. The reduced metabohtes are nthen reoxygenated by monooxygenases back to the parent compound, which can result in an altered ratio of the two enantiomers or epimers. 

Sulindac, also known as sulindac sulfoxide, is a geometric isomer marketed as the cis configuration. It is marketed as a racemate chiral... 

SCHEME 48.12. Fe(III)-catalyzed asymmetric sulfoxidation step for the synthesis of sulindac 23 application of Schiff base chiral ligand 26 and carboxylate additive 27. 

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