Abstract
The use of enantiomerically enriched 4-tolylsulfinyl[2.2]paracyclophane
as a precursor to a variety of mono- and disubstituted [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-tolylsulfinyl[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.’
Key words
asymmetric synthesis - cyclophanes - sulfoxides - enantiomeric resolution
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