Towards a Flexible Strategy for the Synthesis of Enantiomerically Pure (2.2)Paracyclophane Derivatives: The Chemistry of 4-Tolylsulfinyl(2.2)paracyclophane

摘要

The use of enantiomerically enriched 4-tolylsulfi-nyl[2.2]paracyclophane as a precursor to a variety of mono- and di-substituted [2.2]paracyclophane derivatives is described. The goal of our research is to develop a single general precursor that permits the synthesis of the most common [2.2]paracyclophane substitution patterns. The chemistry of two diastereoisomers of 4-tolylsulfi-nyl[2.2]paracyclophane has been explored and it facilitates the synthesis of enantiomerically enriched 4-substituted and 4,13-disubstituted [2.2]paracyclophanes. Directed lithiations result in an unusual cyclisation reaction. Whilst the tolyl group cannot realise our goal, the chemistry outlined acts as a successful 'proof of concept.'