Abstract
The carbanion stabilizing effect induced by the arylsulfonyl group has dominated and typified the chemistry of this functional entity for a long time. In addition to this important feature, the activity of the arylsulfonyl moiety as a leaving group has been exploited and a plethora of exciting synthetic applications have been found. The base- or acid-promoted elimination of the sulfonyl group from of α-amido sulfones and sulfonyl indoles is able to produce the in situ generation of reactive N-acylimino and alkylideneindolenine intermediates that can be used in the diastereo and enantioselective synthesis of various amino and heterocyclic compounds.
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