Enantioselective Preparation of 4-Substituted Cyclohexenes by Radical Fragmentation of Sulfoxides
Organic Letters1999Vol. 1(6), pp. 873–875
Citations Over TimeTop 18% of 1999 papers
Abstract
Radical fragmentation of o-bromophenyl sulfoxides is reported. Starting from enantiomerically pure material, 4-substituted cyclohexene derivatives have been prepared with enantiomeric excesses between 70% and 86%. The key step of the process is a diastereoselective abstraction of a hydrogen atom by the initial aryl radical. The highest enantiomeric exesses have been obtained in the presence of aluminum Lewis acids.
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