Asymmetrische C-C-Knüpfungsreaktionen mit lithiierten Alkyl- und Allylsulfoximinen

Asymmetric C–C–bonding reactions with lithiated alkyl and allyl sulfoximines This thesis deals with the use of (S)-N,S-dimethylphenylsulfoximine in asymmetric synthesis. The lithiated (S)-N,S-dimethylphenylsulfoximine can react with alpha-, beta-unsaturated carbon acid esters. This Michael-type reaction leads to the 1,4-addition products and the so-called tandem products. These tandem products are formed with high diastereoselektivity by addition of one molecule of sulfoximine with two molecules of ester. It was not possible to isolate the pure compounds because the chromatographie led to decomposition. The reaction of lithiated enantiopure cyclohex-1'-enyl-methan-((S)-N-methyl-S-phenylsulfoximine) with aldehydes leads to alpha- and gamma-hydroxyalkylation products depending on the titanation reagent used. While the use of tris-(diethylamino)-titanchlorid leads to beta-hydroxysulfoximines tris-(isopropoxy)-titanchlorid yields delta-hydroxysulfoximines. The products are formed in good yields and with good to excellent diastereoselektivity.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2002

Author dc:creator

• Nienstedt, Sabine

Contributors dc:contributor

• Gais, Hans-Joachim

• info:eu-repo/classification/ddc/540
• Chemie
• Kupplungsreaktion
• Asymmetrische Reaktion
• Kohlenstoff-Kohlenstoff-Bindung
• Lithiumorganische Verbindungen
• Sulfoximide

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

ger

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-121958%22

OAI identifier oai:identifier

oai:publications.rwth-aachen.de:60235