Solid state and solution structural studies of chiral phosphoramide-tin complexes relevant to Lewis base catalyzed aldol reactions

Scott E. Denmark, Xiping Su

Research output: Contribution to journalArticlepeer-review

Abstract

Complexes of chiral phosphoramides 4 and 5 with tin-based Lewis acids were studied by both X-ray crystallography and low temperature 119Sn NMR spectroscopy. The structure of a ternary complex between 5, SnCl4 and benzaldehyde was also obtained and provided a detailed view of the binding of both aldehyde and phosphoramide to Lewis acids. 119Sn NMR, spectroscopy indicated that a 2/1 stoichiometry of phosphoramide to tin is favored in solution as well.

Original languageEnglish (US)
Pages (from-to)8727-8738
Number of pages12
JournalTetrahedron
Volume55
Issue number29
DOIs
StatePublished - Jul 16 1999

Keywords

  • Aldol Reactions
  • Phosphoramides
  • Tin and Compounds
  • X-Ray Crystal Structures

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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