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Title
| - Rhodium Carboxylate Catalyzed Decomposition ofVinyldiazoacetates in the Presence of Heterodienes: Enantioselective Synthesis of the 6-Azabicyclo[3.2.2]nonane and6-Azabicyclo[3.2.2]nonanone Ring Systems
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Abstract
| - Dirhodium tetracarboxylate catalyzed decomposition of vinyldiazoacetates in the presence ofN-phenoxycarbonyl protected 1,2-dihydropyridines or 1-methyl-2-pyridones is a direct method forthe construction of the 6-azabicyclo[3.2.2]nonane ring system. The [3 + 4] cycloaddition occurs bya tandem cyclopropanation/Cope rearrangement. Asymmetric induction is possible in thesetransformations either by using (S)-lactate methyl ester as a chiral auxiliary or dirhodiumtetraprolinates as chiral catalysts.
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