Chiral poisoning in the kinetic resolution of allylic alcohols

J. W. Falle, Makoto Tokunaga

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

Recently, hydrogenations of allylic alcohols using ruthenium catalysts with enantiomerically pure phosphines, such as (R)-BINAP were reported to be useful for the kinetic resolution of cyclic allylic alcohols. These kinetic resolutions can also be effected using racemic BINAP and preferentially deactivating one enantiomer of the catalyst with an enantiomerically pure chiral poison. Poisoning of racemic (BINAP)-RuCl 2 (dmf) x with (1R,2S)-ephedrine provided (R)-2-cyclohexenol in 93% ee at 72% conversion.

Original languageEnglish
Pages (from-to)7359-7362
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number46
DOIs
Publication statusPublished - Nov 12 1993
Externally publishedYes

Fingerprint

Poisoning
Kinetics
Catalyst poisoning
Phosphines
Ephedrine
Catalysts
Hydrogenation
Ruthenium
Enantiomers
Poisons
2-naphthol BINAP
allyl alcohol

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Chiral poisoning in the kinetic resolution of allylic alcohols. / Falle, J. W.; Tokunaga, Makoto.

In: Tetrahedron Letters, Vol. 34, No. 46, 12.11.1993, p. 7359-7362.

Research output: Contribution to journalArticle

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