New C 1- and C 2-symmetric sulfoximines : synthesis and application in enantioselective metal catalysis

In this dissertation, the preparation of new C1- and C2-symmetric sulfoximines (N,N- and P,N-ligands) for enantioselective metal catalysis is described. Guided by the excellent level of enantioselectivity observed using aminosulfoximine in the Cu-catalyzed Mukaiyama-aldol reaction, modifications of this class of potential ligand by substitution of the aryl bridge was effected. Gratifyingly, a methyl-substituted aminosulfoximine proved to be the best ligand of our screening in the Cu-catalyzed carbonyl-ene reaction between pyruvate esters and olefins. Moreover, aminosulfoximines were applied in the Cu-mediated vinylogous Mukaiyama-aldol reaction between pyruvate esters and dienol silanes, affording alpha,beta-unsaturated delta-hydroxy diesters in good yield with enantioselectivities of up to 99% ee.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2006

Author dc:creator

• Rémy, Pauline

Contributors dc:contributor

• Bolm, Carsten

• info:eu-repo/classification/ddc/540
• Chemie
• Katalyse
• Mukaiyama-Reaktion
• Sulfoximinen
• Vinylogous Mukaiyama aldol reaction

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

eng

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-114789%22

OAI record oai:identifier

https://publications.rwth-aachen.de/oai2d?verb=GetRecord&metadataPrefix=oai_dc&identifier=oai%3Apublications.rwth-aachen.de%3A52574