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Access to 2′,3′-dihydro-1′H-spiro[indoline-3,4′-pyridin]-2-ones via amino acid derived phosphine-catalyzed asymmetric [4+2] annulation with easily available oxindole-derived α,β-unsaturated imines

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
70
Issue
17
Identifiers
DOI: 10.1016/j.tet.2014.02.052
Keywords
  • Asymmetric [4+2] Annulation
  • Chiral Phosphines
  • Organocatalysts
  • Spirooxindoles

Abstract

Abstract The phosphine-catalyzed asymmetric [4+2] annulation of vinyl ketones with more easily available oxindole-derived α,β-unsaturated imines has been further developed in the presence of an easily available multifunctional thiourea-phosphine catalyst derived from natural amino acid, providing the enantioselective synthesis of 2′,3′-dihydro-1′H-spiro[indoline-3,4′-pyridin]-2-ones in good yields and moderate de values with higher enantioselectivities under mild conditions.

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