{"id":{"repo_id":"aachen","oai_identifier":"oai:publications.rwth-aachen.de:56524"},"canonical_url":"https://search.dev.ndltd.org/etd/aachen/oai:publications.rwth-aachen.de:56524","repository":{"repo_id":"aachen","name":"RWTH Aachen University","base_url":"https://publications.rwth-aachen.de/oai2d"},"display":{"title":"Synthese chiraler Sulfone aus Sulfoximinen in Lösung und an fester Phase","abstract":"Synthesis of chiral sulfones using sulfoximines in solution and on solid phase Abstract: Allylic sulfoximines were synthesised in a one pot reaction starting from (S)-N,S-dimethylphenylsulfoximine in high yields. The following g-hydroxyalkylation with functionalised aldehydes was achieved with diastereoselectivities >= 96%. Also the a-hydroxyalkylation of lithiiated vinylic sulfoximines were studied. Using the steric more demanding tert-butyldiphenylsilylgroup instead of the methylgroup allowed to increase the diastereomeric excess to 56-80%. Enantiomeric pure sulfones were synthesised with MCBPA using the corresponding sulfoximines with yields >90%. The chirality of the sulfonimidoylgroup was used for the building of chiral molecule structures followed by the conversion in sulfones. The mild reaction conditions tolerated a series of functional groups in the molecule. For the reaction a mechanism was postulated. The use of the sulfonimidoylgroup in the solid phase synthesis was demonstrated with a hydroxyalkylation. The bonding of the sulfoximine to the Merrifield resin was achieved in 91% yield. The cleavage as sulfon was nearly quantitative. The isolated yield was between 81-84%.","abstract_html":"Synthesis of chiral sulfones using sulfoximines in solution and on solid phase Abstract: Allylic sulfoximines were synthesised in a one pot reaction starting from (S)-N,S-dimethylphenylsulfoximine in high yields. The following g-hydroxyalkylation with functionalised aldehydes was achieved with diastereoselectivities >= 96%. Also the a-hydroxyalkylation of lithiiated vinylic sulfoximines were studied. Using the steric more demanding tert-butyldiphenylsilylgroup instead of the methylgroup allowed to increase the diastereomeric excess to 56-80%. Enantiomeric pure sulfones were synthesised with MCBPA using the corresponding sulfoximines with yields >90%. The chirality of the sulfonimidoylgroup was used for the building of chiral molecule structures followed by the conversion in sulfones. The mild reaction conditions tolerated a series of functional groups in the molecule. For the reaction a mechanism was postulated. The use of the sulfonimidoylgroup in the solid phase synthesis was demonstrated with a hydroxyalkylation. The bonding of the sulfoximine to the Merrifield resin was achieved in 91% yield. The cleavage as sulfon was nearly quantitative. 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The following g-hydroxyalkylation with functionalised aldehydes was achieved with diastereoselectivities >= 96%. Also the a-hydroxyalkylation of lithiiated vinylic sulfoximines were studied. Using the steric more demanding tert-butyldiphenylsilylgroup instead of the methylgroup allowed to increase the diastereomeric excess to 56-80%. Enantiomeric pure sulfones were synthesised with MCBPA using the corresponding sulfoximines with yields >90%. The chirality of the sulfonimidoylgroup was used for the building of chiral molecule structures followed by the conversion in sulfones. The mild reaction conditions tolerated a series of functional groups in the molecule. For the reaction a mechanism was postulated. The use of the sulfonimidoylgroup in the solid phase synthesis was demonstrated with a hydroxyalkylation. The bonding of the sulfoximine to the Merrifield resin was achieved in 91% yield. The cleavage as sulfon was nearly quantitative. The isolated yield was between 81-84%."]},{"key":"dc:source","label":"Dc Source","values":["Aachen : Publikationsserver der RWTH Aachen University 214 S. (2001). = Aachen, Techn. Hochsch., Diss., 2001"]},{"key":"dc:title","label":"Title","values":["Synthese chiraler Sulfone aus Sulfoximinen in Lösung und an fester Phase"]}]}],"canonical_facts":{"dc:contributor":["Gais, Hans-Joachim"],"dc:coverage":["DE"],"dc:creator":["Hachtel, Jochen"],"dc:date":["2001"],"dc:description":["Synthesis of chiral sulfones using sulfoximines in solution and on solid phase Abstract: Allylic sulfoximines were synthesised in a one pot reaction starting from (S)-N,S-dimethylphenylsulfoximine in high yields. The following g-hydroxyalkylation with functionalised aldehydes was achieved with diastereoselectivities >= 96%. Also the a-hydroxyalkylation of lithiiated vinylic sulfoximines were studied. Using the steric more demanding tert-butyldiphenylsilylgroup instead of the methylgroup allowed to increase the diastereomeric excess to 56-80%. Enantiomeric pure sulfones were synthesised with MCBPA using the corresponding sulfoximines with yields >90%. The chirality of the sulfonimidoylgroup was used for the building of chiral molecule structures followed by the conversion in sulfones. The mild reaction conditions tolerated a series of functional groups in the molecule. For the reaction a mechanism was postulated. The use of the sulfonimidoylgroup in the solid phase synthesis was demonstrated with a hydroxyalkylation. The bonding of the sulfoximine to the Merrifield resin was achieved in 91% yield. The cleavage as sulfon was nearly quantitative. 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