Asymmetrische Synthese und stereoselektive Substitution allylischer Sulfoximin-funktionalisierter Homoallylalkohole
Enantiopure acyclic (E)- and (Z)-configured allylic sulfoximines have been synthesized from N,S-dimethyl-S-phenylsulfoximine and aldehydes via the addition-elimination-isomerization route. Titanation of lithiated (E)- and (Z)-configured allylic sulfoximines with Chlortrisdiethylanimotitan and subsequent reaction with aldehydes afforded the corresponding alpha-syn-configured homoallylic alcohols with moderate to high regioselectivities and high diastereoselectivities. Copper-mediated subtitution in gamma position of the sulfonimidoyl-group furnished the corresponding (E)-configured allylic alcohols in good yields, with complete regioselectivities and high 1,3-chiraltiy transfer.
info:eu-repo/classification/ddc/540, Chemie, Homoallyl-Verbindungen, Allylalkoholderivate, Sulfoximide, Asymmetrische Synthese, Hydroxyalkylierung, Substitutionsreaktion
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