Asymmetrischer katalytischer Phenyltransfer zur Synthese von Diarylmethanolen und Diarylmethylaminen

Enantiopure diarylmethanols and diarylmethylamines are important intermediates in the synthesis of biologically active compounds, since their derivatives have e. g. antihistaminic properties. For example, the (S)-enantiomer of the commercially important non-sedating antihistamine agent Cetirizine hydrochloride, a diarylmethylamine derivative, displays a better pharmacological profile than the racemate. Despite the importance of these compounds, asymmetric (catalytic) processes for the synthesis of diarylmethanols and especially diarylmethylamines are rather limited. For the synthesis of diarylmethanols, a highly enantioselective catalytic phenyl transfer from a mixed organozinc reagent to aldehydes was developed, employing catalytic amounts of a chiral catalyst precursor. The results of synthetic studies and investigations in order to reveal the nature of the active species in the catalysis by means of low-temperature-NMR- and IR-spectroscopic methods are presented. Previous syntheses of enantiopure diarylmethylamines relied on resolution, stoichiometric amounts of chromium or diastereoselective approaches via chiral auxiliaries. A highly enantioselective catalytic procedure for the addition of diphenylzinc to masked N-formyl-imines employing [2.2]-paracyclophane-based ketimines was developed and is described.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2002

Author dc:creator

• Hermanns, Nina

Contributors dc:contributor

• Bolm, Carsten

• info:eu-repo/classification/ddc/540
• Chemie
• Arylierung
• Asymmetrische Synthese
• Homogene Katalyse
• Zinkorganyle
• Diarylmethanole
• Diarylmethylamine
• Metallocene

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

ger

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-121977%22

OAI identifier oai:identifier

oai:publications.rwth-aachen.de:60254