Titanium-catalyzed diastereoselective epoxidations of ene diols and allylic alcohols with β-hydroperoxy alcohols as novel oxygen donors

W Adam, K Peters, M Renz

Index: Adam, Waldemar; Peters, Karl; Renz, Michael Journal of Organic Chemistry, 1997 , vol. 62, # 10 p. 3183 - 3189

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Citation Number: 24

Abstract

β-Hydroperoxy alcohols 1-4 serve as effective tridentate oxygen donors for the highly diastereoselective, titanium-catalyzed epoxidation of ene diols 5a-e. Thus, in contrast to the bidentate tert-butyl hydroperoxide, the usual oxygen donor employed in Sharpless-type epoxidations and known to work poorly for polyhydroxy substrates, the tridentate β- hydroperoxy alcohols efficiently replace the tridentate epoxy diol products 6a-e in the ...