Frank, Eduard and Flugel, Jana L. and d'Heureuse, Ludwig and Woick, Sophie and Breder, Alexander (2026) Enantioconvergent Synthesis of Diarylmethane Drugs via Privileged Benzhydrol Intermediates. JOURNAL OF ORGANIC CHEMISTRY, 91 (1). pp. 793-797. ISSN 0022-3263, 1520-6904
Full text not available from this repository. (Request a copy)Abstract
The benzhydryl motif is a privileged pharmacophore in antihistaminic and neuroactive drugs. We present a broadly applicable, enantioconvergent synthesis of benzhydrols via asymmetric migratory Tsuji-Wacker oxidation of stilbenes. This constitutionally stereodivergent protocol operates without preactivated or sterically biased substrates, affording chiral alpha,alpha-diaryl ketones in up to 91% ee, which convert to benzhydrols without erosion of stereochemistry. The method enables concise syntheses of (S)-cloperastine and isotopically labeled (S)-diphenhydramine-d 5, establishing chiral benzhydrols as versatile intermediates for redox- and step-economic drug assembly.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ENANTIOSELECTIVE SYNTHESIS; DIPHENHYDRAMINE; ESCITALOPRAM; CETIRIZINE; LEVOCETIRIZINE; ORPHENADRINE; CITALOPRAM; BINDING; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Prof. Dr. Alexander Breder |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 26 Aug 2026 08:34 |
| Last Modified: | 26 Aug 2026 08:34 |
| URI: | https://pred.uni-regensburg.de/id/eprint/65957 |
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