| Abstract
| - A study of the protonation of the cycloadducts derived from the dearomatization reaction of lithiatedN-alkyl-N-benzyldiphenylphosphinamides has been carried out. The regio- and stereoselectivity ofthe process has been analyzed in terms of the size of the N-alkyl substituent, the acidity and sizeof the protonating reagent, and the cosolvent used. The optimization of these variables allowedthe preparation of tetrahydrobenzo[c]-1-aza-2λ5-phospholes containing a 1,3-cyclohexadiene or 1,4-cyclohexadiene system with moderate to excellent regio- and stereocontrol. The heterocycles werereadily hydrolyzed, affording γ-(N-alkylamino)diphenylphosphinic acids with the functionalitieslinked to a cyclohexadiene substructure.
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