Entwicklung und Erweiterung von organokatalytischen Domino-Reaktionen

An organocatalytic quadruple-cascade-reaction between Acetaldehyde and aromatic Nitrostyrenes has been developed. This reaction was conducted in a microwave oven with THF as solvent. The additive was water. With diphenylprolinol-TMS-ether as catalyst, several examples of trisubstituted cyclohexenecarbaldehydes with yileds between 25-45% and ee between 89-99% were synthesized. The diastereomeric ratio was between 1.4:1 and 3.5:1. Another topic was the expansion of a known triplecascade-reaction. This should be expanded via Diels-Alder-Reactions. Therefore, the aldehydes were derivatized with esterlinkages. In a subsequent step, the Diels-Alder-Reactions should be carried out by heating or under catalysis of Lewis-acids. This was not succesful. The third topic was a organocatalytic Tandem-Reaction (Michael/Horner) between a nitrophosphonate and an unsaturated aldehyde. The resulting cyclohexene ester were obtained with yields up to 33% and an ee up to 92%.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2009

Author dc:creator

• Krüll, Ralf

Contributors dc:contributor

• Enders, Dieter

• info:eu-repo/classification/ddc/540
• Organokatalyse
• Tandem-Reaktion
• Kaskade
• Diels-Alder-Reaktion
• Hetero-Diels-Alder-Reaktion
• Homo-Diels-Alder-Reaktion
• Michael-Addition
• Henry-Reaktion
• Horner-Emmons-Reaktion
• Chemie
• Aldol-Reaktion
• Aldol-reaction

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

ger

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-112637%22

OAI record oai:identifier

https://publications.rwth-aachen.de/oai2d?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Apublications.rwth-aachen.de%3A50076