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An expedient one-pot sequential three-component reaction for the stereoselective synthesis of functionalized spiro-sulfamidate imine fused δ-lactone scaffold

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Identifiers
DOI: 10.1016/j.tetlet.2014.06.088
Keywords
  • Organocatalysis
  • Sequential One-Pot
  • Multi-Component Reaction
  • Stereoselective
  • Spiro-Sulfamidate Imine
  • δ-Lactone

Abstract

Abstract A convenient one-pot three-component transformation between 4-aryl-5H-1,2,3-oxathiazole-2,2-dioxides, trans-β-aryl/alkyl-substituted acroleins and paraformaldehyde in CH2Cl2 at room temperature in the presence of commercially available l-proline and DBU as the organocatalysts has been successfully realized for the first time via a Michael-condensation-hemiacetalization sequence process. The resulting functionalized spiro-sulfamidate imine fused δ-lactone scaffolds were obtained via in situ oxidation of spiro-δ-lactols by PCC in good to excellent overall yields and moderate to good diastereomeric ratio (up to ⩽5:1 dr). Moreover, a synthetically useful intermediate trans–cis-β-amino-α-azido compound has been successfully achieved through our procedure.

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