38157-64-1Relevant academic research and scientific papers
Synthesis of Spirocyclic 1-Pyrrolines from Nitrones and Arynes through a Dearomative [3,3′]-Sigmatropic Rearrangement
Alshreimi, Abdullah S.,Anderson, Laura L.,Islam, Shahidul M.,Koto, Nicholas-George,Pe?a, Ricardo L.,Reidl, Tyler W.,Wink, Donald J.,Zhang, Guanqun
, p. 15244 - 15248 (2020)
A dearomative [3,3′]-sigmatropic rearrangement that converts N-alkenylbenzisoxazolines into spirocyclic pyrroline cyclohexadienones has been developed by using the dipolar cycloaddition of an N-alkenylnitrone and an aryne to access these unusual transient rearrangement precursors. This cascade reaction affords spirocyclic pyrrolines that are inaccessible through dipolar cycloadditions of exocyclic cyclohexenones and provides a fundamentally new approach to novel spirocyclic pyrroline and pyrrolidine motifs that are common scaffolds in biologically-active molecules. Diastereoselective functionalization processes have also been explored to demonstrate the divergent synthetic utility of the unsaturated spirocyclic products.
