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Diastereoselective Schenck Ene Reaction of Singlet Oxygen with Chiral AllylicAlcohols; Access to Enantiomerically Pure 1,2,4-Trioxanes
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.ORCID iD: 0000-0002-5543-2041
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2009 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 65, no 41, 8531-8537 p.Article in journal (Refereed) Published
Abstract [en]

A series of antimalarial chiral 1,2,4-trioxanes (1–8) were synthesised in high enantiomeric purities. Enantioselective addition of R2Zn reagent to 3-methyl-2-butenal catalysed by (+)-MIB or (−)-MIB yielded both the enantiomers of the chiral allylic alcohols 9–11 (90–98% ee), which were subjected to diastereoselective photooxygenation in the presence of tetraphenylporphine (TPP) to obtain (R,R)-threo- or (S,S)-threo-β-hydroperoxy alcohols (12–14). Reaction of β-hydroperoxy alcohols (12–14) with different cyclic ketones produced optically active trioxanes 1–8.

 

 

Place, publisher, year, edition, pages
2009. Vol. 65, no 41, 8531-8537 p.
Keyword [en]
Chiral trioxanes; Antimalarial; Hydroperoxides; Endoperoxides; Allylic alcohols; MIB
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-7298DOI: 10.1016/j.tet.2009.08.020ISI: 000270345900012Scopus ID: 2-s2.0-69549096060OAI: oai:DiVA.org:miun-7298DiVA: diva2:127188
Available from: 2008-12-02 Created: 2008-12-02 Last updated: 2016-09-29Bibliographically approved

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Sabbani, SunilHedenström, Erik
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CiteExportLink to record
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Citation style
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