Alkene anti-dihydroxylation with malonoyl peroxides

Carla Alamillo-Ferrer, Stuart C. Davidson, Michael J. Rawling, Natalie H. Theodoulou, Matthew Campbell, Philip G. Humphreys, Alan R. Kennedy, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Malonoyl peroxide 1, prepared in a single step from the commercially available diacid, is an effective reagent for the anti-dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of acetic acid at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (35-92%) with up to 13:1 anti-selectivity. A mechanism consistent with experimental findings is proposed that accounts for the selectivity observed.

LanguageEnglish
Pages5132-5135
Number of pages4
JournalOrganic Letters
Volume17
Issue number20
DOIs
Publication statusPublished - 16 Oct 2015

Fingerprint

Peroxides
Alkenes
peroxides
alkenes
selectivity
acetic acid
Acetic Acid
reagents
hydrolysis
Hydrolysis

Keywords

  • anti-Dihydroxylation
  • Malonoyl Peroxides
  • alkenes
  • alkaline hydrolysis

Cite this

Alamillo-Ferrer, C., Davidson, S. C., Rawling, M. J., Theodoulou, N. H., Campbell, M., Humphreys, P. G., ... Tomkinson, N. C. O. (2015). Alkene anti-dihydroxylation with malonoyl peroxides. Organic Letters, 17(20), 5132-5135. https://doi.org/10.1021/acs.orglett.5b02674
Alamillo-Ferrer, Carla ; Davidson, Stuart C. ; Rawling, Michael J. ; Theodoulou, Natalie H. ; Campbell, Matthew ; Humphreys, Philip G. ; Kennedy, Alan R. ; Tomkinson, Nicholas C. O. / Alkene anti-dihydroxylation with malonoyl peroxides. In: Organic Letters. 2015 ; Vol. 17, No. 20. pp. 5132-5135.
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Alamillo-Ferrer, C, Davidson, SC, Rawling, MJ, Theodoulou, NH, Campbell, M, Humphreys, PG, Kennedy, AR & Tomkinson, NCO 2015, 'Alkene anti-dihydroxylation with malonoyl peroxides' Organic Letters, vol. 17, no. 20, pp. 5132-5135. https://doi.org/10.1021/acs.orglett.5b02674

Alkene anti-dihydroxylation with malonoyl peroxides. / Alamillo-Ferrer, Carla; Davidson, Stuart C.; Rawling, Michael J.; Theodoulou, Natalie H.; Campbell, Matthew; Humphreys, Philip G.; Kennedy, Alan R.; Tomkinson, Nicholas C. O.

In: Organic Letters, Vol. 17, No. 20, 16.10.2015, p. 5132-5135.

Research output: Contribution to journalArticle

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T1 - Alkene anti-dihydroxylation with malonoyl peroxides

AU - Alamillo-Ferrer, Carla

AU - Davidson, Stuart C.

AU - Rawling, Michael J.

AU - Theodoulou, Natalie H.

AU - Campbell, Matthew

AU - Humphreys, Philip G.

AU - Kennedy, Alan R.

AU - Tomkinson, Nicholas C. O.

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N2 - Malonoyl peroxide 1, prepared in a single step from the commercially available diacid, is an effective reagent for the anti-dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of acetic acid at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (35-92%) with up to 13:1 anti-selectivity. A mechanism consistent with experimental findings is proposed that accounts for the selectivity observed.

AB - Malonoyl peroxide 1, prepared in a single step from the commercially available diacid, is an effective reagent for the anti-dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of acetic acid at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (35-92%) with up to 13:1 anti-selectivity. A mechanism consistent with experimental findings is proposed that accounts for the selectivity observed.

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Alamillo-Ferrer C, Davidson SC, Rawling MJ, Theodoulou NH, Campbell M, Humphreys PG et al. Alkene anti-dihydroxylation with malonoyl peroxides. Organic Letters. 2015 Oct 16;17(20):5132-5135. https://doi.org/10.1021/acs.orglett.5b02674