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Asymmetric reduction of functionalized ketones and their synthetic applications
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Fang, Zhijia (Researcher in chemistry) (2013) Asymmetric reduction of functionalized ketones and their synthetic applications. PhD thesis, University of Warwick.
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WRAP_THESIS_Fang_2013.pdf - Submitted Version Download (8Mb) | Preview |
Official URL: http://webcat.warwick.ac.uk/record=b2704341~S1
Abstract
Asymmetric transfer hydrogenation (ATH) represents a powerful methodology for the
synthesis of chiral secondary alcohols. The synthesis of chiral propargylic alcohols by
asymmetric transfer hydrogenation of acetylenic ketones has been applied to a number of
applications including target oriented synthesis.
In this thesis, the asymmetric transfer hydrogenation of a large number of functionalized
alkyones and dialkyones has been fully investigated. Basic principles as well as detailed
reaction conditions for the ATH of acetylenic ketones have been established. Chiral
propargylic alcohols have been successfully prepared by a new method that was
developed during this project and some of the products and strategies were used for the
total synthesis of (-)-yashabushidiol B and panaxjapyne A.
Moreover a group of aromatic ketones functionalized with the 1,3-dioxin-4-one scaffold
were prepared and used as substrates for asymmetric transfer hydrogenation. Detailed
reaction conditions such as catalyst loading, temperature, substitution effects and stability
of substrates were fully investigated. Reduced products were prepared in a highly
stereoselective manner and the utility of this method and the resulting chiral alcohols have
been illustrated by the total synthesis of yashabushitriol.
The application of ATH to the preparation of a highly optically pure ester for scanning
tunnelling microscopy (SCM) dissociation and hierarchical assembly was also undertaken.
| Item Type: | Thesis (PhD) |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Library of Congress Subject Headings (LCSH): | Ketones, Reduction (Chemistry), Hydrogenation, Asymmetry (Chemistry), Alcohols -- Synthesis, Chirality |
| Official Date: | December 2013 |
| Institution: | University of Warwick |
| Theses Department: | Department of Chemistry |
| Thesis Type: | PhD |
| Publication Status: | Unpublished |
| Supervisor(s)/Advisor: | Wills, Martin |
| Extent: | vi, 260 leaves : illustrations. |
| Language: | eng |
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