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- Sabbani, Sunil, et al.
(författare)
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Diastereoselective Schenck Ene Reaction of Singlet Oxygen with Chiral AllylicAlcohols; Access to Enantiomerically Pure 1,2,4-Trioxanes
- 2009
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Ingår i: Tetrahedron. - : Elsevier BV. - 0040-4020 .- 1464-5416. ; 65:41, s. 8531-8537
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Tidskriftsartikel (refereegranskat)abstract
- 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.
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