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Title: The synthesis of solid-supported cyclohexan-1,3-dione (CHD) and its applications as a solid-phase reagent
Author: Humphrey, Cara Emily
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2003
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Combinatorial chemistry has had a major impact on organic chemistry, enabling the synthesis of thousands of compounds in parallel, using state-of-art robotics for synthesis, purification and analysis. The benefits are most evident in the pharmaceutical industry where there is a high demand for novel compounds as drug candidates. Library synthesis relies greatly on the use of solid-supported reagents or scavenger resins which afford ease of purification and isolation of the required product. The synthesis of multifunctional cyclohexane-1,3-dione (CHD) I on polystyrene resin, using microwave irradiation in a key step is described. CHD resin I was used for the ‘capture and release’ of a library of amides where both resin acylation and amide release were also accelerated using microwave irradiation. CHD resin was also used as an allyl-cation scavenger resin in the palladium-catalysed deprotection of O-Alloc-alcohols. (Fig. 8497) The preparation of enantiomerically pure compounds is an ongoing challenge for organic chemistry and is especially important in the preparation of drug candidates. CHD resin underwent lipase-catalysed ‘capture and release’, demonstrating an unusual reversal of selectivity. In each case the predominant enantiomer observed was the (R)-(-)-3-phenylbutyryl acryl group rather than the expected (S)-enantiomer, despite the fact that the hydrolases under study showed exclusive selectivity for the (S)-enantiomer in the corresponding solution-phase hydrolysis reactions. The use of dimedone 1,3-enol esters for the screening of hydrolase activity by UV/V is detection of copper-dimedone chelates is also described.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available