| Abstract
| - Enantiopure aromatic (phenyl, naphthyl) and heteroaromatic (pyridyl, quinolyl, diazinyl) sulfoxides havebeen synthesized by reaction of (S)-tert-butyl tert-butanethiosulfinate with aryl- or heteroaryllithiumderivatives. The ortho-directed metalation of the sulfoxides was performed with lithium bases. Subsequentaddition of the lithiated intermediates to N-tosylimines afforded tosylaminoalkyl tert-butylsulfinyl arenes.In most cases a complete asymmetric induction was highlighted in favor of (S,S) isomers. Heating theaminosulfoxides provided an original cyclization to form novel cyclic sulfenamides. A novel enantiopuresynthesis of a benzylamine was described. An application of an enantiopure aminosulfoxide as N,S ligandfor the asymmetric catalysis of allylic nucleophilic substitution has been successfully tested.
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