Asymmetric catalysis with water

Efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis

Makoto Tokunaga, Jay F. Larrow, Fumitoshi Kakiuchi, Eric N. Jacobsen

Research output: Contribution to journalArticle

1204 Citations (Scopus)

Abstract

Epoxides are versatile building blocks for organic synthesis. However, terminal epoxides are arguably the most important subclass of these compounds, and no general and practical method exists for their production in enantiomerically pure form. Terminal epoxides are available very inexpensively as racemic mixtures, and kinetic resolution is an attractive strategy for the production of optically active epoxides, given an economical and operationally simple method. Readily accessible synthetic catalysts (chiral cobalt-based salen complexes) have been used for the efficient asymmetric hydrolysis of terminal epoxides. This process uses water as the only reagent, no added solvent, and low loadings of a recyclable catalyst (<0.5 mole percent), and it affords highly valuable terminal epoxides and 1,2-diols in high yield with high enantiomeric enrichment.

Original languageEnglish
Pages (from-to)936-938
Number of pages3
JournalScience
Volume277
Issue number5328
DOIs
Publication statusPublished - 1997 Aug 15
Externally publishedYes

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Epoxy Compounds
Catalysis
Hydrolysis
Water
Synthetic Chemistry Techniques
Cobalt

ASJC Scopus subject areas

  • General

Cite this

Asymmetric catalysis with water : Efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis. / Tokunaga, Makoto; Larrow, Jay F.; Kakiuchi, Fumitoshi; Jacobsen, Eric N.

In: Science, Vol. 277, No. 5328, 15.08.1997, p. 936-938.

Research output: Contribution to journalArticle

Tokunaga, Makoto ; Larrow, Jay F. ; Kakiuchi, Fumitoshi ; Jacobsen, Eric N. / Asymmetric catalysis with water : Efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis. In: Science. 1997 ; Vol. 277, No. 5328. pp. 936-938.
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