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Enantioselective transformations of α-diazocarbonyl compounds; catalyst and substrate effects
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Date
2016
Authors
Ring, Aoife
Journal Title
Journal ISSN
Volume Title
Publisher
University College Cork
Published Version
Abstract
The primary objective of this thesis was an extensive investigation into transition metal catalysed intramolecular C–H insertion reactions of α-diazoacetamides and intramolecular aromatic addition reactions of α-diazoketones. Exploration of the effect of substrate structure and the impact of various aspects of the catalyst complex was undertaken to determine which has a greater influence on the ensuing C–H insertion and aromatic addition reactions. While particular attention was paid to copper-bisoxazoline catalyst complexes, studies were also conducted, although to a lesser extent, using the more widely studied achiral and chiral rhodium catalysts. Significantly, use of the copper complexes in C–H insertion reactions of α-diazoacetamides resulted in formation of γ-lactams and β-lactams in high enantiopurities, 91% ee and 83% ee, while copper catalysed aromatic addition reactions resulted in formation of azulenones in up to 92% ee.
Description
Keywords
C-H insertion , Copper catalysis , Diazocarbonyl , Lactams , Sulfones , Buchner reaction , Rhodium catalysis , Enantioselective , Bisoxazoline
Citation
Ring, A. 2016. Enantioselective transformations of α-diazocarbonyl compounds; catalyst and substrate effects. PhD Thesis, University College Cork.