Understanding the correlation of structure and selectivity in the chiral-phosphoramide-catalyzed enantioselective allylation reactions: Solution and solid-state structural studies of bisphosphoramide·SnCl4 complexes

Scott E Denmark, Jiping Fu

Research output: Contribution to journalArticle

Abstract

Complexation of bisphosphoramides, linked by various length methylene tethers, with tin tetrachloride was studied by both solution NMR spectroscopy and single-crystal X-ray crystallography. The formation of cis-configured, octahedral 1/1 bisphosphoramide·SnCl4 complexes was supported by both crystallographic and solution NMR studies. In addition, the formation of such complexes was shown to be highly dependent on the tether length and solution concentration. Single-crystal X-ray analysis of bisphosphoramide·SnCl4 complexes also provided detailed information on the stereochemical environment relevant to the enantioselectivity of asymmetric allylation reactions.

Original languageEnglish (US)
Pages (from-to)2208-2216
Number of pages9
JournalJournal of the American Chemical Society
Volume125
Issue number8
DOIs
StatePublished - Feb 26 2003

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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