Synthese chiraler Sulfone aus Sulfoximinen in Lösung und an fester Phase

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%.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2001

Author dc:creator

• Hachtel, Jochen

Contributors dc:contributor

• Gais, Hans-Joachim

• info:eu-repo/classification/ddc/540
• Chemie
• Sulfone
• Asymmetrische Synthese
• Sulfoximide
• Synthon

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

ger

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-118619%22

OAI record oai:identifier

https://publications.rwth-aachen.de/oai2d?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Apublications.rwth-aachen.de%3A56524