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.
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.
Davies
Huw M L
HM
Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York 14260, USA. hadavies@acsu.buffalo.edu
Hodges
L Mark
LM
D000085:Acetates; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002264:Carboxylic Acids; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds; D012238:Rhodium; D013329:Structure-Activity Relationship
D000085:Acetates; D019086:Bridged Bicyclo Compounds, Heterocyclic; D002264:Carboxylic Acids; D009942:Organometallic Compounds; D012238:Rhodium