Untersuchungen zur diastereo- und enantioselektiven Synthese von Matsuon und asymmetrische Synthese von anti-1,2-Sulfanylaminen

The first part of the thesis deals with Matsuone ((2E,4E,6R,10R)-4,6,10,12-Tetramethyltridecan-2,4-dien-7-one), which is the female sex pheromone of the pine scales Matsucoccus-resinosae, M.-matsumurae and M.-thunbergianae. There are different approaches towards the diastereo- und enantioselektive synthesis of the desired natural product described using the SAMP- /RAMP-hydrazone method. Several chiral building blocks were synthesized in high diastereomeric and enantiomeric excesses but the title compound could not be obtained. In the second part of the thesis a flexible diastereo- and enantioselective synthesis of various 1,2-anti-sulfanyl amines (de, ee >= 96%) is described. Starting from alpha-sulfanylated acetaldehyde-SAMP-hydrazone the anti-configured products were obtained in a three- or four-step procedure. Keysteps are the highly diastereoselective alpha-Alkylation of acetaldehyde-SAMP-hydrazone with various electrophiles and the following 1,2-addition to the C-N double bond using different alkylcerium nucleophiles. After removal of the auxiliary by cleavage of the N-N-bond the resulting amines could be isolated or converted to the corresponding benzyl carbamates.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2002

Author dc:creator

• Schaadt, Annette

Contributors dc:contributor

• Enders, Dieter

• 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-119002%22

OAI identifier oai:identifier

oai:publications.rwth-aachen.de:56927