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Title: Development of enantioselective and catalytic cyclisation reactions using hypervalent iodine compounds
Author: Kamouka, Somaia Taher
ISNI:       0000 0004 6494 8028
Awarding Body: University of Huddersfield
Current Institution: University of Huddersfield
Date of Award: 2017
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In this thesis, iodoarene and chiral iodoarene reagents have been developed and used catalytically in the enantioselective cyclisation reaction of unsaturated esters, amides and β-amidoketones. The results in this thesis are divided into three parts. In the first part, the development of the catalytic enantioselective cyclisation of 4-methoxy but-3-enyl benzoate to the 3-hydroxytetrahydrofuran ester using enantiomerically pure chiral hypervalent iodine reagents generated in situ is described. A good enantioselectivity of 77% ee was obtained with moderate yield. In the second part, the development of catalytic conditions for the cyclisation of N-alkenylarylamides induced by iodoarenes leading to the formation of different ring sizes is demonstrated. In addition, the catalytic enantioselective cyclisation of N-alkenylarylamides employing chiral iodoarenes giving dihydrooxazines in good yields and moderate enantioselectivities of up to 64% is achieved. In the third part, the catalytic cyclisation of both propargyl amides and β-amidoketones using 2-iodoanisole to afford 2-oxazolines in good yields is described. Moreover, the catalytic enantioselective cyclisation of β-amidoketones using several chiral iodoarenes is detailed but, unfortunately almost no enantioselectivities was observed.
Supervisor: Moran, Wesley Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry