Towards conformationally-locked difluorosugar analogues: an unexpected sense of dihydroxylation

John Fawcett, Gerry A Griffiths, Jonathan Percy, Stephane Pintat, Clive A Smith, Neil S Spencer, Emi Uneyama

Research output: Contribution to journalArticle

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Abstract

Difluorinated cyclooctenones, synthesised using RCM, can be used as templates for stereoselective oxidative transformations to products that undergo transannular reactions to afford conformationally-locked analogues of 2-deoxy-2,2-difluorosugars with different stereochemical relationships between the C-2 and C-3 hydroxyl groups.
Original languageEnglish
Pages (from-to) 302-303
Number of pages2
JournalChemical Communications
Volume2004
Issue number3
DOIs
Publication statusPublished - 2004

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Hydroxyl Radical

Keywords

  • difluorosugar analogues
  • difluorinated cyclooctenones
  • hydroxyl groups

Cite this

Fawcett, J., Griffiths, G. A., Percy, J., Pintat, S., Smith, C. A., Spencer, N. S., & Uneyama, E. (2004). Towards conformationally-locked difluorosugar analogues: an unexpected sense of dihydroxylation. Chemical Communications, 2004(3), 302-303 . https://doi.org/10.1039/b313813e
Fawcett, John ; Griffiths, Gerry A ; Percy, Jonathan ; Pintat, Stephane ; Smith, Clive A ; Spencer, Neil S ; Uneyama, Emi. / Towards conformationally-locked difluorosugar analogues : an unexpected sense of dihydroxylation. In: Chemical Communications. 2004 ; Vol. 2004, No. 3. pp. 302-303 .
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Fawcett, J, Griffiths, GA, Percy, J, Pintat, S, Smith, CA, Spencer, NS & Uneyama, E 2004, 'Towards conformationally-locked difluorosugar analogues: an unexpected sense of dihydroxylation', Chemical Communications, vol. 2004, no. 3, pp. 302-303 . https://doi.org/10.1039/b313813e

Towards conformationally-locked difluorosugar analogues : an unexpected sense of dihydroxylation. / Fawcett, John; Griffiths, Gerry A; Percy, Jonathan; Pintat, Stephane; Smith, Clive A; Spencer, Neil S; Uneyama, Emi.

In: Chemical Communications, Vol. 2004, No. 3, 2004, p. 302-303 .

Research output: Contribution to journalArticle

TY - JOUR

T1 - Towards conformationally-locked difluorosugar analogues

T2 - an unexpected sense of dihydroxylation

AU - Fawcett, John

AU - Griffiths, Gerry A

AU - Percy, Jonathan

AU - Pintat, Stephane

AU - Smith, Clive A

AU - Spencer, Neil S

AU - Uneyama, Emi

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AB - Difluorinated cyclooctenones, synthesised using RCM, can be used as templates for stereoselective oxidative transformations to products that undergo transannular reactions to afford conformationally-locked analogues of 2-deoxy-2,2-difluorosugars with different stereochemical relationships between the C-2 and C-3 hydroxyl groups.

KW - difluorosugar analogues

KW - difluorinated cyclooctenones

KW - hydroxyl groups

U2 - 10.1039/b313813e

DO - 10.1039/b313813e

M3 - Article

VL - 2004

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EP - 303

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

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Fawcett J, Griffiths GA, Percy J, Pintat S, Smith CA, Spencer NS et al. Towards conformationally-locked difluorosugar analogues: an unexpected sense of dihydroxylation. Chemical Communications. 2004;2004(3): 302-303 . https://doi.org/10.1039/b313813e