Intramolecular [3 + 2]-cycloaddition reaction of push-pull dipoles across heteroaromatic pi-systems.
[reaction: see text] Push-pull dipoles generated from the Rh(II)-catalyzed reaction of diazo imides containing tethered heteroaromatic rings undergo successful [3 + 2]-cycloaddition across the 2,3-pi-bond to provide novel pentacyclic compounds in good to excellent yields in a stereocontrolled fashion. The facility of the cycloaddition is critically dependent on conformational factors in the transition state.
Mejía-Oneto
José M
JM
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Padwa
Albert
A
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D014747:Vinblastine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D014748:Vinca Alkaloids / Q000737:chemistry; D014750:Vincristine / Q000138:chemical synthesis
D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D014748:Vinca Alkaloids; C009667:vindoline; D014750:Vincristine; D014747:Vinblastine; D012428:Ruthenium; C017836:catharanthine