Struktur, Hydroxyalkylierung und Aminoalkylierung von Titanaallylsulfoximinen: Enantioselektive Synthese ungesättigter Alpha-Aminosäuren

Structure, Hydroxyalkylation and Aminoalkylation of Titanaallylsulfoximines: Enantioselective Synthesis of Unsaturated alpha-Amino Acids Enantiopure E- and Z-allylic sulfoximines were lithiated and transmetallated with ClxTi(OR)4-x to give bis(2-alkenyl)titanium(IV)-complexes. These complexes reacted regio- und diastereoselective with aldehydes in gamma-position to yield delta- resp. beta-N-methylsulfonimidoyl-substituted homoallylic alcohols. This reaction and the structures of the titanium(IV)-complexes were examined in detail. Furthermore it was found, that these complexes reacted regio- and diastereoselective with N-sulfonylimino acetic acid esters to yield gamma,delta-unsaturated alpha-amino acid derivatives. The N-sulfonyl-protecting-group could be cleaved under mild conditions. The N-methylsulfonimidoyl-protecting-group was substituted using a diphenylzinc / Ni(dppp)Cl2 mediated cross-coupling-reaction. Thus a concept for the synthesis of beta,delta-substituted gamma,delta-unsaturated alpha-amino acids was developed.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2002

Author dc:creator

• Schleusner, Marcel

Contributors dc:contributor

• Gais, Hans-Joachim

• info:eu-repo/classification/ddc/540
• Chemie

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

ger

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-118944%22

OAI record oai:identifier

https://publications.rwth-aachen.de/oai2d?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Apublications.rwth-aachen.de%3A56865