Chirale Tris(amido)titanaallylsulfoximine: Stereoselektive Hydroxyalkylierung, Struktur und Dynamik

This thesis deals with stereoselective hydroxyalkylation reactions of E- and Z-configured allylic sulfoximines. Titanation of lithiated allylic sulfoximines with chlorotrisdiethylaminotitan and subsequent reaction of the resulting mono(2-alkenyl)tris(diethylamido)titan(IV)-complexes with aldehydes yielded the corresponding beta-N-methylsulfonimidoyl-substituted homoallylic alcohols with moderate to high regio- and excellent diastereoselectivities. Besides synthetic optimization and structural analysis of the hydroxyalkylation products extensive structural investigations of the mono(2-alkenyl)tris(diethylamido)titan(IV)-complexes and mechanistic studies were carried out. The equilibrium of several mono(2-alkenyl)titan(IV)complexes is crucial for the regio- and stereoselectivity of the hydroxyalkylation reaction. Furthermore nitrogen substituted allylic sulfoximines were prepared and investigated in respect of their reactivity and selectivity in hydroxyalkylation reactions. Thus, a concept for alpha-hydroxyalkylation reactions of allylic sulfoximines could be developed.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2003

Author dc:creator

• Bruns, Peter Richard

Contributors dc:contributor

• Gais, Hans-Joachim

• info:eu-repo/classification/ddc/540
• Titanorganische Verbindungen
• Sulfoximide
• Allylgruppe
• Hydroxyalkylierung
• Regioselektivität
• Chemie
• Allylische Sulfoximine
• Titan
• Homoallylalkohole
• stereoselektive Synthes

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

ger

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-123563%22

OAI identifier oai:identifier

oai:publications.rwth-aachen.de:61959