Stereoselective Synthesis of Dithia[3.3]cyclophane S,S%26apos;-Dioxides with Planar and Central Chirality

作者：Barattucci Anna^*; Di Gioia Maria Luisa; Leggio Antonella; Minuti Lucio; Papalia Teresa; Siciliano Carlo; Temperini Andrea; Bonaccorsi Paola

来源：European Journal of Organic Chemistry, 2014, 2014(10): 2099-2104.

DOI：10.1002/ejoc.201301636

• Cyclophanes
• Sulfur heterocycles
• Chirality
• Reactive intermediates

5,8-Dimethyl-1,12-dimethylene-2,11-dithia[3.3]cyclophane 2,11-dioxides with planar and central chirality were synthesized in high yields, starting from 2,5-dimethyl-1,4-benzenedimethanethiol, through the formation of suitable transient sulfenic functions that add to the triple bonds of disubstituted benzenes. Experimental observations allowed mechanistic and stereochemical insights into the key step of the synthetic pathway, and NMR experiments were diagnostic for the structure assignments of the cage-like compounds. The stereochemical characteristics of the new dithiacyclophane S,S-dioxides synthesized may be applicable in the field of organocatalysis.

• 出版日期2014-4