Chiral lithium amides: reactivity studies and applications to target synthesis

Prestly, Mark Robert (2013). Chiral lithium amides: reactivity studies and applications to target synthesis. University of Birmingham. Ph.D.

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Chiral lithium amide bases allow the desymmetrisation of prochiral substrates and the production of enantiomerically enriched products, which are vital for the pharmaceutical industry and the total synthesis of natural products. Chapter 1 gives a brief review of this area and the progress that has been achieved over the last three decades.

In Chapter 2 deprotonation of a ketone and an imide substrate using both chiral and achiral bases is described. Within the development of catalytic chiral lithium amide base methodology, competition reactions (Chapter 3) and lithium exchange experiments (Chapter 4) were carried out between two amine species. It was found that there were appreciable differences in the rate of deprotonation of the substrate between the lithium amides studied.

Chapter 5 describes the design and synthesis of new fluorinated chiral diamines which we hoped could be used as effective chiral lithium amide bases in sub-stoichiometric amounts.

Initial work was also carried out on the total synthesis of the diterpenoid alkaloid concavine. A chiral lithium amide base was used to introduce asymmetry into the synthetic route and the synthesis of the fused oxazepane ring moiety was completed (Chapter 6).

Type of Work: Thesis (Doctorates > Ph.D.)
Award Type: Doctorates > Ph.D.
College/Faculty: Colleges (2008 onwards) > College of Engineering & Physical Sciences
School or Department: School of Chemistry
Funders: Engineering and Physical Sciences Research Council
Subjects: Q Science > QD Chemistry


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