Synthesis of novel tricyclic and tetracyclic sultone scaffolds via 
intramolecular 1,3-dipolar cycloaddition reactions.

Ghandi, M.; Taheri, A.; Bozcheloei, A. H.; Abbasi, A.; Kia, R.

doi:10.1016/j.tet.2012.02.053

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Synthesis of novel tricyclic and tetracyclic sultone scaffolds via intramolecular 1,3-dipolar cycloaddition reactions.

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Kia, R.
Research Group of Structural Dynamics of (Bio)Chemical Systems, MPI for Biophysical Chemistry, Max Planck Society;

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Ghandi, M., Taheri, A., Bozcheloei, A. H., Abbasi, A., & Kia, R. (2012). Synthesis of novel tricyclic and tetracyclic sultone scaffolds via intramolecular 1,3-dipolar cycloaddition reactions. Tetrahedron, 68(18), 3641-3648. doi:10.1016/j.tet.2012.02.053.

Cite as: http://hdl.handle.net/11858/00-001M-0000-002C-2479-3

Abstract

The initially prepared 2-formylphenyl-(E)-2-phenylethenesulfonates from the condensation of (E)-2-phenylethenesulfonyl chloride with 2-hydroxybenzaldehyde derivatives underwent intramolecular [3+2] cycloaddition with methyl or phenylhydroxylamine, sarcosine, and l-proline, affording the corresponding novel isoxazolidine, pyrrolidine and pyrrolizidine-annulated γ,δ-benzo-δ-sultones, respectively, in good yields. Unambiguous assignment of the molecular structures was carried out by single-crystal X-ray diffraction.