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Rh2(OAc)4 catalyzed substrate selective [4+2]/[2+2] cycloaddition of acylketenes: a highly chemo- and regioselective synthesis of spiro(oxindolyl)oxazinones and β-lactams

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
53
Issue
19
Identifiers
DOI: 10.1016/j.tetlet.2012.02.106
Keywords
  • Rhodium(Ii) Acetate
  • Cyclicketimines
  • Acylketenes
  • Diazocarbonyl Compounds
  • Spiroxazinones
  • Spiro-β-Lactams

Abstract

Abstract A rhodium(II) catalyzed [4+2]/[2+2] cycloaddition reaction of N-protected isatin-3-arylimine with acylketene derived from α-diazocarbonyl compounds has been achieved for the first time for the preparation of a novel class of spiro(oxindolyl)oxazinone and spiro(oxindolyl)-β-lactam derivatives.

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