Towards novel atropisomeric triazole-containing organocatalysts

Meloni, Fernanda (2021). Towards novel atropisomeric triazole-containing organocatalysts. University of Birmingham. Ph.D.

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Abstract

Atropisomerism is a type of axial chirality displayed by compounds whose rotation is restricted about an axis. Atropisomeric compounds have shown unique properties in many fields, including drug discovery and catalysis. The vast majority of these compounds are six-membered biaryl or heterobiaryl ring derivatives, and atropisomeric species featuring smaller rings have received much less attention. Nonetheless, they have been successfully employed in numerous asymmetric transformations.

This thesis outlines the synthesis of a novel class of atropisomeric triazole-containing compounds whose potential applications lie within the organocatalytic realm. The experiments detailed in the following chapters will show the scope and limitations of different synthetic approaches, which led to defined syntheses of two distinct generations of triazoles and triazolium salts. Computational calculations, NMR spectroscopy and/or HPLC analyses will reveal that the rotation may be significantly restricted, thus in principle, allowing access to single atropisomers of these chiral compounds. Preliminary results in asymmetric organocatalysis will finally highlight their potential.

Type of Work: Thesis (Doctorates > Ph.D.)
Award Type: Doctorates > Ph.D.
Supervisor(s):
Supervisor(s)EmailORCID
Fossey, J.S.UNSPECIFIEDorcid.org/0000-0002-2626-5117
Davies, PaulUNSPECIFIEDUNSPECIFIED
Licence: All rights reserved
College/Faculty: Colleges (2008 onwards) > College of Engineering & Physical Sciences
School or Department: School of Chemistry
Funders: Other
Other Funders: University of Birmingham
Subjects: Q Science > QD Chemistry
URI: http://etheses.bham.ac.uk/id/eprint/11930

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