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

研究成果: Article査読

1327 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)936-938
ページ数3
ジャーナルScience
277
5328
DOI
出版ステータスPublished - 1997 8月 15
外部発表はい

ASJC Scopus subject areas

  • 一般

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