Preparation of α-aminophosphines on solid support: Model studies and parallel synthesis

B. Bar Nir Ben-Aroya, Moshe Portnoy

Research output: Contribution to journalArticlepeer-review

Abstract

On-resin assembly of phosphine ligands represents a formidable challenge. Following model solution studies, we developed two synthetic routes for α-aminophosphine synthesis on solid support. The ligands are prepared via the Mannich reaction of the resin-bound aldehyde, amine and diphenylphosphine with very good yield and purity. Alternatively, the amine can serve as the anchoring building block. The ligands were qualitatively and quantitatively analyzed using gel-phase 31P and 13C NMR techniques. The studies culminated in the parallel synthesis of a 40-member library of borane-protected α-aminophosphines.

Original languageEnglish
Pages (from-to)5147-5158
Number of pages12
JournalTetrahedron
Volume58
Issue number25
DOIs
StatePublished - 17 Jun 2002

Keywords

  • Aminophosphines
  • Combinatorial chemistry
  • Mannich reaction
  • Solid-phase synthesis

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