Diastereoselective schenck ene reaction of singlet oxygen with chiral allylic alcohols; access to enantiomerically enriched 1,2,4-trioxanes

Autor:	Paul M. O'Neill, John Bacsa, Erik Hedenström, Sunil Sabbani, Louise La Pensee
Rok vydání:	2009
Předmět:	chemistry.chemical_classification Allylic rearrangement Ketone Chemistry Organic Chemistry Enantioselective synthesis Biochemistry Reagent Drug Discovery Organic chemistry Photooxygenation Enantiomer Enantiomeric excess Ene reaction
Zdroj:	Tetrahedron. 65:8531-8537
ISSN:	0040-4020
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6090651a2ea9b4c837f65871423ed44b https://doi.org/10.1016/j.tet.2009.08.020 Zobrazit plný text záznamu Full Text from ScienceDirect