1067238-03-2Relevant academic research and scientific papers
Functionalization and rearrangement of spirocyclohexadienyl oxindoles: Experimental and theoretical investigations
Rousseau, Geraldine,Robert, Frederic,Landais, Yannick
, p. 11160 - 11173 (2009)
The preparation and functionalization of spirocyclohexa-2,5diene oxindoles is described. The spirocyclic core of the title compounds was installed by using a SmI2-mediated cyclization of aryl iodobenzamides. Epoxidation with CF3COsu
Rearrangement of spirocyclic oxindoles with lithium amide bases
Rousseau, Geraldine,Robert, Frederic,Schenk, Kurt,Landais, Yannick
supporting information; experimental part, p. 4441 - 4444 (2009/05/07)
(Chemical Equation Presented) Spirocyclohexa-2,5-dienes were shown to rearrange at -40 °C, when treated with 1 equiv of LDA. Alkyl halides and aldehydes then reacted with the resulting phenanthridinone lithium enolate intermediates, with distinct regioselectivities and high diastereocontrol, to afford functionalized dearomatized phenanthridinones which were elaborated further. A mechanistic scheme involving a diisopropylamine-mediated proton transfer was proposed to rationalize the rearrangement.
