Monoacylation of unprotected symmetrical diamines with resin-bound benzoic acids

Yonghui Wang, Jian Jin, Michael L. Moore, Todd L. Graybill, Feng Wang, Michelle A. Wang, Bing Wang, Qian Jin, Ralph A. Rivero

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8 Scopus citations

Abstract

Control of diamine concentration was critical for efficient monoacylation of diverse symmetrical 1°and 2°cyclic/acyclic diamines. A protocol for monoacylation of unprotected symmetrical diamines with a resin-bound benzoic acid is described. The nature of the resin (gel-based polystyrene vs highly crosslinked macroporous polystyrene) was found to play a minor role in acylation selectivity. Rather, the concentration of the diamine dictates the ratio of mono- and diacylated products. Thus, by employing a high concentration of symmetrical diamine (e.g., 1 M, 20 equiv), monoacylation can be selectively achieved for a variety of unprotected symmetrical alkyl and aryl diamines.

Original languageEnglish
Pages (from-to)6645-6648
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number35
DOIs
StatePublished - 23 Aug 2004
Externally publishedYes

Keywords

  • Concentration effect
  • Crosslinking
  • Diacylation
  • Monoacylation
  • Resin comparison
  • Solid phase reaction
  • Symmetrical diamines

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