Synthesis of Spirocyclic 1-Pyrrolines from Nitrones and Arynes through a Dearomative [3,3′]-Sigmatropic Rearrangement
Abdullah S. Alshreimi
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
These authors contributed equally to this work.
Search for more papers by this authorGuanqun Zhang
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
These authors contributed equally to this work.
Search for more papers by this authorTyler W. Reidl
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
Search for more papers by this authorRicardo L. Peña
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
Search for more papers by this authorNicholas-George Koto
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
Search for more papers by this authorDr. Shahidul M. Islam
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
Search for more papers by this authorDr. Donald J. Wink
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
Search for more papers by this authorCorresponding Author
Prof. Laura L. Anderson
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
Search for more papers by this authorAbdullah S. Alshreimi
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
These authors contributed equally to this work.
Search for more papers by this authorGuanqun Zhang
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
These authors contributed equally to this work.
Search for more papers by this authorTyler W. Reidl
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
Search for more papers by this authorRicardo L. Peña
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
Search for more papers by this authorNicholas-George Koto
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
Search for more papers by this authorDr. Shahidul M. Islam
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
Search for more papers by this authorDr. Donald J. Wink
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
Search for more papers by this authorCorresponding Author
Prof. Laura L. Anderson
Department of Chemistry, University of Illinois at Chicago, 845 W Taylor Street, Chicago, IL, USA
Search for more papers by this authorAbstract
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.
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