Abstract
The reaction of two optically active 1-alkyl-3,4-diallyloxypyrrolidine 1 oxides, (9) and (15), under basic conditions has been examined. The 1-benzyl derivative (9), on reaction with lithium diisopropylamide, furnished a single pyrrolidine derivative (11) by intramolecular 1,3-dipolar cycloaddition of an N-benzylidene azomethine ylide (10), while the 1 -methyl derivative (15) reacted with tert-butyllithium in the presence of trimethylaluminum to afford only a single 7-azabicyclo[2.2.1]heptane derivative (19) by spontaneous intramolecular 1,3-dipolar cycloaddition of the endocyclic azomethine ylide (17)
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