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.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2001

Author dc:creator

• Giesen, Nicole

Contributors dc:contributor

• Gais, Hans-Joachim

• info:eu-repo/classification/ddc/540
• Chemie
• Homoallyl-Verbindungen
• Allylalkoholderivate
• Sulfoximide
• Asymmetrische Synthese
• Hydroxyalkylierung
• Substitutionsreaktion

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

ger

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-124314%22

OAI identifier oai:identifier

oai:publications.rwth-aachen.de:62814