Pd-katalysierte asymmetrische Synthese allylischer Sulfone und Stereochemie der Lithiumsalze chiraler allylischer Alpha-tert-Butylsulfonyl-Carbanionen

The Pd(0)-catalyzed allylic sulfonation of allylic substrates with Lithium tert-Butylsulfinate in presence of chiral bisphospines leads to chiral allylic tert-Butylallylsulfones in high yields up to 96% and selectivities up to 98%. Deprotonation of said compounds in alpha-position to their sulfonyl-group forms alpha-tert-Butylsulfonylcarbanions, which are characterized by a hindered rotation around the alpha-C-S-bond and consequently configurative stability at appropriately low temperatures. Last-named renders the chiral anionic species capable for enantioselective C-C-bond formation with reactive electrophiles. The present work particularly deals with structural investigations of Lithium salts of alpha-tert-Butylsulfonylcarbanions in crystal as well as in solution and with the approximation and improvement of their configurative stability.

Grantor dc:publisher

Publikationsserver der RWTH Aachen University

Year dc:date

2000

Author dc:creator

• Gerhards, Frank

Contributors dc:contributor

• Gais, Hans-Joachim

• info:eu-repo/classification/ddc/540
• Chemie
• Sulfone
• Allylgruppe
• Asymmetrische Synthese
• Palladium
• Katalysator
• Lithiumorganische Verbindungen
• Butylgruppe
• Stereochemie

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

ger

Identifier

https://publications.rwth-aachen.de/search?p=id:%22RWTH-CONV-123621%22

OAI identifier oai:identifier

oai:publications.rwth-aachen.de:62023