Beneficial effect of ortho-methoxy groups in the asymmetric ring opening of meso epoxides with silicon tetrachloride catalyzed by chiral ortho-methoxyphenyldiazaphosphonamide Lewis bases

Scott E Denmark, Thomas Wynn, Bradley G. Jellerichs

Research output: Contribution to journalArticle

Abstract

The reported ability of chiral phosphonamide 1 to effect the enantioselective opening of meso epoxides with silicon tetrachloride has not withstood experimental verification by Denmark's group. Having reexamined the ring-opening of cyclooctene oxide (see scheme), Denmark and co-workers found a serious discrepancy between their results (81-83% recovery of the episode and an essentially racemic product) and those reported by Buono et al. (77% yield and >99% ee).

Original languageEnglish (US)
Pages (from-to)2255-2256
Number of pages2
JournalAngewandte Chemie - International Edition
Volume40
Issue number12
DOIs
StatePublished - Jun 18 2001

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Keywords

  • Asymmetric catalysis
  • Correspondence
  • Epoxides
  • Lewis bases
  • Ring opening

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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