STEREOSELECTIVE EPOXIDATION OF ALLYLIC ALCOHOLS AND DEHYDROGENATIVE OXIDATION OF SECONDARY ALCOHOLS BY MEANS OF t-BUTYL HYDROPEROXIDE AND ALUMINIUM REAGENTS.

Kazuhiko Takai, Koichiro Oshima, Hitosi Nozaki

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Treatment of a solution of geraniol and (t-BuO)//3Al in benzene with t-BuOOH at 5 degree C gives (2R*, 3R*)-2,3-epoxy-3,7-dimethyl-6-octenyl acetate in 83% yield after acetylative workup. Eight allylic alcohols are converted to alpha , beta -epoxy alcohols in preparative yields. The epoxidation of secondary (E)-allylic alcohols shows opposite stereo-selectivities to t-BuOOH-VO(acac)//2 system. Asymmetric epoxidation with a chiral hydroxamic acid as a ligand gives unsatisfactory degrees of enantiomeric excess. The same system can also convert secondary alcohols into ketones in excellent yields, while primary ones react very slowly.

Original languageEnglish
Pages (from-to)3791-3795
Number of pages5
JournalBulletin of the Chemical Society of Japan
Volume56
Issue number12
DOIs
Publication statusPublished - Jan 1 1983
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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