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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Lewis Bases
Epoxy Compounds
Oxides
Recovery
Silicon
silicon tetrachloride

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

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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).",
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T1 - Beneficial effect of ortho-methoxy groups in the asymmetric ring opening of meso epoxides with silicon tetrachloride catalyzed by chiral ortho-methoxyphenyldiazaphosphonamide Lewis bases

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AU - Wynn, Thomas

AU - Jellerichs, Bradley G.

PY - 2001/6/18

Y1 - 2001/6/18

N2 - 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).

AB - 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).

KW - Asymmetric catalysis

KW - Correspondence

KW - Epoxides

KW - Lewis bases

KW - Ring opening

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