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Diastereoselective ...
Diastereoselective Schenck Ene Reaction of Singlet Oxygen with Chiral AllylicAlcohols; Access to Enantiomerically Pure 1,2,4-Trioxanes
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- Sabbani, Sunil (author)
- Mittuniversitetet,Institutionen för naturvetenskap, teknik och matematik (-2012)
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La Pensée, Louise (author)
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Bacsa, John (author)
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- Hedenström, Erik (author)
- Mittuniversitetet,Institutionen för naturvetenskap, teknik och matematik (-2012)
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O´Neill, Paul M (author)
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(creator_code:org_t)
- Elsevier BV, 2009
- 2009
- English.
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In: Tetrahedron. - : Elsevier BV. - 0040-4020 .- 1464-5416. ; 65:41, s. 8531-8537
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
Close
- 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.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Keyword
- Chiral trioxanes; Antimalarial; Hydroperoxides; Endoperoxides; Allylic alcohols; MIB
- Chemistry
- Kemi
Publication and Content Type
- ref (subject category)
- art (subject category)
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