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Domino condensation/aza-Michael/O→N acyl migration of carbodiimides with activated α,β-unsaturated carboxylic acids to form hydantoins

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
44
Issue
47
Identifiers
DOI: 10.1016/j.tetlet.2003.09.134
Keywords
  • Hydantoins
  • Domino Reaction
  • Aza-Michael
  • Carbodiimides

Abstract

Abstract Activated α,β-unsaturated carboxylic acids undergo an unexpected domino condensation/aza-Michael/O→N acyl migration with carbodiimides, producing N, N-disubstituted hydantoins in good yields. An array of structurally varied aspartic acid-derived hydantoins, including some fluorinated derivatives, have been synthesized by this method, whose scope and limits are discussed.

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