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The epoxy-Ramberg-Backlund reaction (ERBR): A sulfone-based method for the synthesis of allylic alcohols

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JournalEuropean Journal of Organic Chemistry
DatePublished - 27 Mar 2006
Issue number7
Number of pages15
Pages (from-to)1740-1754
Original languageEnglish

Abstract

The epoxy-Ramberg-Backlund reaction (ERBR) is outlined, in which alpha,beta-epoxy sulfones are converted into a range of mono-, di- and tri-substituted allylic alcohols, on treatment with base. Modification of this method enabled the preparation of enantio-enriched allylic alcohols following the diastereoselective epoxidation of enantio-enriched vinyl sulfones that were accessed efficiently from the chiral pool. The scope, optimisation and limitations of the ERBR as a method for the preparation of allylic alcohols are discussed. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006.

    Research areas

  • epoxy-Ramberg-Backlund reaction, allylic alcohols, vinyl sulfones, nucleophilic epoxidation, VINYL SULFONES, NUCLEOPHILIC EPOXIDATION, ALPHA,BETA-UNSATURATED SULFONES, ASYMMETRIC EPOXIDATION, CARBONYL-COMPOUNDS, ORGANIC-SYNTHESIS, REDUCTION, KETONES, CYCLOPENTENONES, ALDEHYDES

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