Synthesis of Enantiomerically Pure Bis‐Sulfinyl Substituted Phenylene Ethynylenes |
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| Authors: | Anna Barattucci Maria Chiara Aversa Elisa Deni Teresa Papalia Paola Bonaccorsi |
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| Affiliation: | 1. Dipartimento di Scienze Chimiche, Viale F. Stagno d'Alcontres 31,Università di Messina, IT‐98166 Messina;2. Dipartimento di Scienze del Farmaco e Prodotti per la Salute, Università di Messina, Villaggio SS. Annunziata, IT‐98168 Messina (phone: +39‐090‐6565172;3. fax: +39‐090‐6765166) |
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| Abstract: | The stereoselective and efficient monoaddition of transient [(1S,2R,4R)‐2‐hydroxy‐7,7‐dimethylbicyclo[2.2.1]hept‐1‐yl]methanesulfenic (=(1S)‐isoborneol‐10‐sulfenic) acid to isomeric diethynylbenzenes affords {1‐[(1S)‐isoborneol‐10‐sulfinyl]ethenyl}ethynylbenzenes. Their enantiomerically pure (RS)‐epimers are involved in a Cu‐free Sonogashira coupling with 1,4‐diiodo‐2,5‐dimethoxybenzene to give C2‐symmetric bis‐sulfinyl phenylene ethynylenes, stimulating prototypes of new sulfurated chiral architectures that can find application as chelating agents. |
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| Keywords: | Sulfenic acids Sonogashira coupling Phenylene ethynylenes Sulfoxides syn‐Addition |
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