Alkene anti-Dihydroxylation with Malonoyl Peroxides

Alkene anti-Dihydroxylation with Malonoyl Peroxides

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 u...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2015-10, Vol.17 (20), p.5132-5135
Hauptverfasser: Alamillo-Ferrer, Carla, Davidson, Stuart C, Rawling, Michael J, Theodoulou, Natalie H, Campbell, Matthew, Humphreys, Philip G, Kennedy, Alan R, Tomkinson, Nicholas C. O
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
Alkenes - chemistry
Biological Products - chemistry
Indicators and Reagents
Malonates - chemistry
Molecular Structure
Peroxides - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02674