Synthesis and application of stereogenic nitrogen-containing ammonium salts as phase-transfer catalysts

Dutton, Mark Jason (2016). Synthesis and application of stereogenic nitrogen-containing ammonium salts as phase-transfer catalysts. University of Birmingham. Ph.D.

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Abstract

The chirality of nitrogen was at the forefront of chemistry over 110 years ago. Since then it has been widely under-acknowledged as a potential chirality source in organic synthesis. This thesis demonstrates the diastereoselective formation of stereogenic nitrogen-containing ammonium salts. Over 150 compounds were synthesised and employed as phase-transfer catalysts in order to assess the chiral-at-nitrogen influence on the outcome of two common phase-transfer-catalysed reactions. Several X-ray crystal structures of single diastereoisomer chiral-at-nitrogen ammonium salts were isolated as well as the synthesis of a library of secondary and tertiary amines.

Type of Work: Thesis (Doctorates > Ph.D.)
Award Type: Doctorates > Ph.D.
Supervisor(s):
Supervisor(s)EmailORCID
Fossey , J.S.UNSPECIFIEDUNSPECIFIED
Preece, Jon AndrewUNSPECIFIEDUNSPECIFIED
Licence:
College/Faculty: Colleges (2008 onwards) > College of Engineering & Physical Sciences
School or Department: School of Chemistry
Funders: None/not applicable
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
URI: http://etheses.bham.ac.uk/id/eprint/6755

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