Heterocycles p. 1519 - 1522 (1992)
Update date:2022-08-05
Topics:
Takano, Seiichi
Sugihara, Yoshiaki
Ogasawara, Kunio
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 azomethane ylide (17).
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