Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Stereoselective Epoxidation of Allylic Alcohols and Dehydrogenative Oxidation of Secondary Alcohols by Means of t-Butyl Hydroperoxide and Aluminium Reagents
Kazuhiko TakaiKoichiro OshimaHitosi Nozaki
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1983 Volume 56 Issue 12 Pages 3791-3795

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Abstract

Treatment of a solution of geraniol and (t-BuO)3Al in benzene with t-BuOOH at 5 °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 α,β-epoxy alcohols in preparative yields. The epoxidation of secondary (E)-allylic alcohols shows opposite stereoselectivities 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.

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