Authors: Huw M. L. Davies and L. Mark Hodges
J. Org. Chem.,
2002, 67 (16), 5683–5689
Dirhodium tetracarboxylate catalyzed decomposition of vinyldiazoacetates in the presence of N-phenoxycarbonyl protected 1,2-dihydropyridines or 1-methyl-2-pyridones is a direct method for the construction of the 6-azabicyclo[3.2.2]nonane ring system. The [3 + 4] cycloaddition occurs by a tandem cyclopropanation/Cope rearrangement. Asymmetric induction is possible in these transformations either by using (S)-lactate methyl ester as a chiral auxiliary or dirhodium tetraprolinates as chiral catalysts.