Synthesis of new recoverable catalysts and their application in asymmetric reduction of ketimines with trichlrosilane

Figlus, Marek (2008) Synthesis of new recoverable catalysts and their application in asymmetric reduction of ketimines with trichlrosilane. PhD thesis, University of Glasgow.

Abstract

Obtaining chiral amines from ketones via imine intermediates represents an attractive strategy that opens a straightforward route to valuable building blocks for the pharmaceutical and other fine chemicals industries. Metal-free oranocatalysis can be viewed as an attractive and broadly applicable methodology in which the metal is not vital for the key bond-forming event. Previously developed in our laboratory, N-methylvaline-derived formamides IIIa,b proved to be efficient catalysts for asymmetric reduction of prochiral ketimines with trichlorosilane, (up to 98%, 95% ee).136,137 Tagging the catalyst to a fluorous ponytail IIIc, soluble and insoluble polymers IIId, or gold nanoparticles IIIe simplified the isolation procedure, while preserving high activities and stereoselectivities (up to 98%, 91% ee). The recovered catalysts could be reused at least 5 times without the loss of activity or stereoselectivity. This technology appears to be particularly suited to the small-scale parallel chemistry.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Subjects: Q Science > QD Chemistry
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Kocovsky, Prof. Pavel
• Date of Award: 2008
• Depositing User: Mrs Marie Cairney
• Unique ID: glathesis:2008-1640
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 05 Mar 2010
• Last Modified: 10 Dec 2012 13:44
• URI: http://theses.gla.ac.uk/id/eprint/1640