Regio-and stereocontrolled synthesis of epoxy alcohols and triols from allylic and homoallylic alcohols via iodocarbonates

A Bongini, G Cardillo, M Orena, G Porzi…

Index: Bongini, Alessandro; Cardillo, Giuliana; Orena, Mario; Porzi, Gianni; Sandri, Sergio Journal of Organic Chemistry, 1982 , vol. 47, # 24 p. 4626 - 4633

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Citation Number: 106

Abstract

The regio-and stereoselective synthesis of cyclic iodo carbonates 1-10, resulting from allylic and homoallylic alcohols, was investigated. These useful intermediates were easily hydrolyzed to epoxy alcohols 11-20 or triols 21-30, depending on the polymeric reagent employed (Amberlyst A 26 in the OH-or C032-form, respectively). Stereochemical assignments were carried out by 13C NMR or'H NMR correlations and by conversion of ...

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