121. Rhodium Carboxylate Catalyzed Decomposition of Vinyldiazoacetates in the Presence of Heterodienes:  Enantioselective Synthesis of the 6-Azabicyclo[3.2.2]nonane and 6-Azabicyclo[3.2.2]nonanone Ring Systems

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.

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