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

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The epoxy-Ramberg-Backlund reaction (ERBR): A sulfone-based method for the synthesis of allylic alcohols. / Evans, P ; Johnson, P ; Taylor, R J K .

In: European Journal of Organic Chemistry, No. 7, 27.03.2006, p. 1740-1754.

Research output: Contribution to journalArticle

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Evans, P, Johnson, P & Taylor, RJK 2006, 'The epoxy-Ramberg-Backlund reaction (ERBR): A sulfone-based method for the synthesis of allylic alcohols', European Journal of Organic Chemistry, no. 7, pp. 1740-1754. https://doi.org/10.1002/ejoc.200500956

APA

Evans, P., Johnson, P., & Taylor, R. J. K. (2006). The epoxy-Ramberg-Backlund reaction (ERBR): A sulfone-based method for the synthesis of allylic alcohols. European Journal of Organic Chemistry, (7), 1740-1754. https://doi.org/10.1002/ejoc.200500956

Vancouver

Evans P, Johnson P, Taylor RJK. The epoxy-Ramberg-Backlund reaction (ERBR): A sulfone-based method for the synthesis of allylic alcohols. European Journal of Organic Chemistry. 2006 Mar 27;(7):1740-1754. https://doi.org/10.1002/ejoc.200500956

Author

Evans, P ; Johnson, P ; Taylor, R J K . / The epoxy-Ramberg-Backlund reaction (ERBR): A sulfone-based method for the synthesis of allylic alcohols. In: European Journal of Organic Chemistry. 2006 ; No. 7. pp. 1740-1754.

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@article{6f46cd9a59da4619b1b4192cec8ca817,
title = "The epoxy-Ramberg-Backlund reaction (ERBR): A sulfone-based method for the synthesis of allylic alcohols",
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.",
keywords = "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",
author = "P Evans and P Johnson and Taylor, {R J K}",
year = "2006",
month = "3",
day = "27",
doi = "10.1002/ejoc.200500956",
language = "English",
pages = "1740--1754",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-VCH Verlag",
number = "7",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - The epoxy-Ramberg-Backlund reaction (ERBR): A sulfone-based method for the synthesis of allylic alcohols

AU - Evans, P

AU - Johnson, P

AU - Taylor, R J K

PY - 2006/3/27

Y1 - 2006/3/27

N2 - 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.

AB - 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.

KW - epoxy-Ramberg-Backlund reaction

KW - allylic alcohols

KW - vinyl sulfones

KW - nucleophilic epoxidation

KW - VINYL SULFONES

KW - NUCLEOPHILIC EPOXIDATION

KW - ALPHA,BETA-UNSATURATED SULFONES

KW - ASYMMETRIC EPOXIDATION

KW - CARBONYL-COMPOUNDS

KW - ORGANIC-SYNTHESIS

KW - REDUCTION

KW - KETONES

KW - CYCLOPENTENONES

KW - ALDEHYDES

U2 - 10.1002/ejoc.200500956

DO - 10.1002/ejoc.200500956

M3 - Article

SP - 1740

EP - 1754

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 7

ER -