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Communication | Regular issue | Vol 34, No. 8, 1992, pp.1519-1522
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6107
First Example of Intramolecular 1,3-Dipolar Cycloaddition of Non-stabilized Azomethine Ylide Generated from Tertiary Amine N-Oxide

Seiichi Takano,* Yoshiaki Sugihara, and Kunio Ogasawara

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980, Japan


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).